Supporting Information. Contents

Save this PDF as:
 WORD  PNG  TXT  JPG

Size: px
Start display at page:

Download "Supporting Information. Contents"

Transcription

1 Supporting Information Rhodium-Catalyzed Selective Mono- and Di-Amination of Arenes with Single Directing Site On Water Md Ashif Ali,, Xiayin Yao,, Guigen Li, and Hongjian Lu, * Contents Schemes S1-S9...2 General Methods... 3 General Procedure for the Preparation of Starting Materials... 4 General Procedure for the Rh-Catalyzed Amidation with Azides Spectroscopic Data of Compounds Obtained in this Study (Schemes 2-3) General Procedure for the diamination Spectroscopic Data of Compounds Obtained in diamination (Scheme 4)...32 One-pot reaction Reactivity Study of Mono-amination (Schemes S1-S4) Preliminary Mechanistic Study (Scheme 5 and Scheme S5) Kinetic Experiments (Schemes S6-S9)...39 References Spectra

2 Schemes S1-S9 2

3 General Methods Unless otherwise stated, all commercial reagents and solvents were used without additional purification. Analytical thin layer chromatography (TLC) was performed on pre-coated silica gel GF254 plates. Visualization on TLC was achieved by the use of UV light (254 nm). Column chromatography was undertaken on silica gel ( mesh) using a proper eluent. 1 H NMR was recorded on FT AM 400 (400 MHz). Chemical shifts were quoted in parts per million (ppm) referenced to the appropriate solvent peak. The following abbreviations were used to describe peak splitting patterns when appropriate: br = broad, s = singlet, d = doublet, t = triplet, q = quartet, dd = doublet of doublet, td = triplet of doublet, ddd = doublet of doublet of doublet, m = multiplet. Coupling constants, J, were reported in hertz (Hz). 13 C NMR was recorded on FT AM 400 (100 MHz) and was fully decoupled by broad band proton decoupling. Chemical shifts were reported in ppm referenced to the appropriate solvent peak. Infrared (IR) spectra were recorded neat in 0.5 mm path length using a KBr. Frequencies are given in reciprocal centimeters (cm-1) and only selected absorbance is reported. High resolution mass spectra were obtained from the UHD Accurate-Mass Q-TOF. 3

4 General Procedure for the Preparation of Starting Materials Arylpyridines General procedure for the preparation of arylpyridines 1a-1k [2] Aryl pyridines were prepared according to reference [2]. A mixture of heteroaryl bromide (2.0 mmol), arylboronic acid (3.0 mmol), Pd(OAc) 2 (1.5 mol %), K 3 PO 4 7H 2 O (4.0 mmol) in mixture of isopropanol (10 ml) and water (10 ml) was stirred at 80 C for indicated time. The mixture was added to brine (40 ml) and extracted four times with ethyl acetate (25 ml x 4), the solvent was evaporated in 4

5 vacuo and the product was isolated by short column chromatography. A mixture of 3-(pyridin-2-yl)phenol (119.8 mg, 0.7 mmol), 4-methylbenzenesulfonyl chloride (267.0 mg, 1.4 mmol) and K 2 CO 3 (193.5 mg, 1.4 mmol) in CH 3 CN (8 ml) were refluxed at 125 C for 40 h. The mixture was washed by water and extracted with dichloromethane. The solvent was evaporated in vacuo and the crude reaction mixture was purified by chromatography on silica gel (4:1 n-hexane/etoac) as an eluent to give the 79.7 mg (0.25 mmol) brown oil. Yield 35%, R f = 0.3 (4:1 n-hexane/etoac); 1 H NMR (400 MHz, CDCl 3 ) δ 8.65 (d, J = 4.2 Hz, 1H), 7.90 (d, J = 7.9 Hz, 1H), (m, 3H), (m, 1H), 7.59 (d, J = 8.0 Hz, 1H), 7.36 (t, J = 8.0 Hz, 1H), 7.30 (d, J = 8.1 Hz, 2H), 7.23 (ddd, J = 7.4, 4.9, 0.8 Hz, 1H), 6.98 (dd, J = 8.1, 1.6 Hz, 1H), 2.42 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , 21.63; HRMS (ESI) ([M+H] + ) calcd. for C 18 H 15 NO 3 S, , found A solution of 3-(pyridin-2-yl)phenol (87.3 mg, 0.51 mmol) in 2 ml of dichloromethane was prepared. To this solution was added pyridine (87.0 mg, 1.1 mmol) and the solution was cooled in an ice-salt bath. To this solution was added a solution of trifluoromethanesulfonic anhydride (437.3 mg, 1.55 mmol) in 3 ml of dichloromethane drop wise. The reaction was allowed to warm slowly and was complete after 2 hours. Water and dichloromethane were added and the layers were separated. The aqueous layer was extracted with dichloromethane. The organic extracts were dried over magnesium sulfate, filtered and evaporated to a residue. The 5

6 residue was purified by silica gel column chromatography (5:1 n-hexane/etoac) and mg (0.43 mmol) of a clear liquid (85% yield) was obtained. R f = 0.33 (3:1 n-hexane/etoac); 1 H NMR (400 MHz, CDCl 3 ) δ 8.70 (d, J = 4.5 Hz, 1H), (m, 2H), 7.77 (td, J = 7.7, 1.7 Hz, 1H), 7.71 (d, J = 7.9 Hz, 1H), 7.53 (t, J = 8.2 Hz, 1H), (m, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , (q, J = Hz); HRMS (ESI) ([M+H] + ) calcd. for C 12 H 8 F 3 NO 3 S, , found (3-((tert-butyldimethylsilyl)oxy)phenyl)pyridine was synthesize as reference [1d] : 3-(pyridin-2-yl)phenol 3 (171.2 mg, 1.0 mmol) with tert-butyldimethylchlorosilane (226.1 mg, 1.5 mmol) and imidazole (129.4 mg, 1.9 mmol) in CH 2 Cl 2 (5 ml) were stirred for 24 h. Silica gel chromatography (eluent:hexane/etoac = 30/1) of the crude product afforded the title compound as colorless oil (142.8 mg, 0.5 mmol 50%). R f = 0.50 (hexane/etoac = 5/1). The starting material 1k was prepared according to general procedure. Yield 96% (359.4 mg, 1.92 mmol), yellow oil, R f = 0.46 (hexane). 1 H NMR (400 MHz, CDCl 3 ) δ 8.54 (d, J = 2.9 Hz, 1H), 7.79 (s, 1H), (m, 2H), 7.43 (td, J = 8.4, 2.9 Hz, 1H), 7.36 (t, J = 7.6 Hz, 1H), 7.23 (d, J = 7.5 Hz, 1H), 2.44 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ (d, J = 254.3), (d, J = 3.9 Hz), , ,

7 (d, J = 23.5 Hz), , , , , (d, J = 18.5 Hz), (d, J = 4.2 Hz), Procedure for the Preparation of 2-phenylpyrimidine 1l [1h] A mixture of 2-chloropyrimidine (229.0 mg, 2.0 mmol), phenylboronic acid (365.7 mg, 3.0 mmol), Pd(OAc) 2 (3.4 mg, 1.5 mol %), K 3 PO 4 7H 2 O (1.35 g, 4.0 mmol) in mixture of isopropanol (10 ml) and water (10 ml) was stirred at 80 C for indicated time. The mixture was added to brine (40 ml) and extracted four times with ethyl acetate (25 ml x 4), the solvent was evaporated in vacuo and the crude product was purfied by short column chromatography to form desired product mg (1.6 mmol, 80%) Procedure for the Preparation of (E)-1-phenylethan-1-one O-methyl oxime 1m [1i] To a solution of acetophenone (0.61 g, 5 mmol) in ethanol (10 ml), and H 2 O (25 ml) was added NaOAc (2.72 g, 20 mmol) followed by methoxyamine hydrochloride (1.25 g, 15 mmol) under air. The reaction mixture was stirred in a pre-heated oil bath at 80 o C for 12 h and then cooled to room temperature. To the reaction mixture H 2 O (10 ml) was added, extracted by EtOAc for three times, dried over MgSO 4 and evaporated in vacuum to afford the product (0.495 g, 3.3 mmol, 66%) without any further purification. Preparation of 6-aryl substituted purine derivative 1n [1j-k] 7

8 Procedure for Step I In an oven dried round bottom flask (25 ml), free hydroxyl starting material (143.4 mg, 0.5 mmol) was taken and then dry acetonitrile (7 ml) was added followed by acetic anhydride (255.2 mg, 2.5 mmol), triethyl amine (347 μl, 2.5 mmol) and 4-dimethylaminopyridine (6.1 mg, 0.05 mmol) were added respectively and stirred for 16 h at room temperature. Then methanol (1 ml) was added stirred for additional 1 h. The solvent was evaporated under reduced pressure and crude was purified by silica gel column using hexane and ethyl acetate as eluent to form desired 207 mg (0.5 mmol, 100%). Procedure for Step II The product obtained from Step I was transferred to a oven dried Schlenk tube followed by phenylboronic acid (121.9 mg, 1.0 mmol), K 2 CO 3 (103.7 mg, 0.75 mmol) and Pd(PPh 3 ) 4 (57.8 mg, 5 mol %) were added and refilled with nitrogen gas. Then toluene (5 ml) was added crewed with Teflon cap and stirred on a preheated oil bath for 10 h. After cooling to room temperature, the mixture was transferred into a round bottom flask and solvent was evaporated under reduced pressure and crude was purified by silica gel column using hexane and ethyl acetate as eluent. (2R,3S,4S,5R)-2-(acetoxymethyl)-5-(6-phenyl-9H-purin-9-yl)tetrahydrofuran-3,4- diyl diacetate 1n: Yield 79% (0.4 mmol, mg) colorless gummy, R f = 0.48 (hexane/etoac = 5/1). 1 H NMR (400 MHz, CDCl 3 ) δ 9.03 (s, 1H), 8.75 (dd, J = 7.9, 1.6 Hz, 2H), 8.28 (s, 1H), 7.56 (q, J = 6.3 Hz, 3H), 6.30 (d, J = 5.3 Hz, 1H), 6.02 (t, J = 5.4 Hz, 1H), (m, 1H), (m, 2H), 4.40 (dd, J = 12.9, 5.1 Hz, 1H), 2.16 (s, 3H), 2.14 (s, 3H), 2.09 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , 86.38, 80.39, 73.08, 70.65, 63.05, 21.54, 20.75, 20.53,

9 Aryl Azides General Procedure for the Preparation of Aryl Azides In a 20 ml scintillation vial, aromatic amines (2.0 mmol, 1.0 equiv) was dissolved in 15 ml of HOAc and 8 ml of H 2 O and chilled in an ice bath. NaNO 2 (207.0 mg, 3.0 mmol, 1.5 equiv) was added slowly, and the resulting mixture was stirred at 0 C for one hour. NaN 3 (208.0 mg, 3.2 mmol, 1.6 equiv) was then added slowly, and the resulting mixture was warmed to ambient temperature, and stirred for 1 hour. The solution was diluted with 30 ml of water and 30 ml of CH 2 Cl 2 and basified by the slow addition of K 2 CO 3 until bubbling ceased. The phases were separated and the aqueous phase was extracted with an additional 3 20 ml of CH 2 Cl 2. The combined organic phases were washed with water (25 ml x 4) and brine (25 ml x 1). The 9

10 resulting organic phase was dried over Na 2 SO 4 and filtered. The filtrate was concentrated in vacuum and purified by column chromatography. The compound was prepared following the general procedure. Yield 90% (503.1 mg, 1.8 mmol), brown oil, R f = 0.9 (hexane/etoac = 40/1). 1 H NMR (400 MHz, CDCl 3 ) δ 7.77 (d, J = 2.3 Hz, 1H), 7.36 (dd, J = 8.6, 2.3 Hz, 1H), 7.05 (d, J = 8.6 Hz, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , The compound was prepared following the general procedure. Yield 95% (704.5 mg, 1.9 mmol, 95% purity), yellow solid, R f = 0.78 (hexane/etoac = 5/1). 1 H NMR (400 MHz, CDCl 3 ) δ 8.06 (d, J = 1.9 Hz, 1H), 7.63 (dd, J = 8.4, 1.9 Hz, 1H), 6.85 (d, J = 8.4 Hz, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , 88.97, In a 20 ml scintillation vial, 2,6-dibromo-4-methylaniline (208.0 mg, 2.0 mmol, 1.0 equiv) was dissolved in 15 ml of HOAc and 8 ml of H 2 O and chilled in an ice bath. NaNO 2 (207.0 mg, 3.0 mmol, 1.5 equiv) was added slowly, and the resulting mixture was stirred at 0 C for one hour. NaN 3 (208.0 mg, 3.2 mmol, 1.6 equiv) was then added slowly, and the resulting mixture was warmed to ambient temperature, and stirred for 1 hour. The solution was diluted with 30 ml of water and 30 ml of CH 2 Cl 2 10

11 and basified by the slow addition of K 2 CO 3 until bubbling ceased. The phases were separated and the aqueous phase was extracted with an additional 3 20 ml of CH 2 Cl 2. The combined organic phases were washed with water (25 ml x 4) and brine (25 ml x 1). The resulting organic phase and dried over Na 2 SO 4 and filtered. The filtrate was concentrated in vacuo and purified by column chromatography. Yield 90% (523.7 mg, 1.8 mmol), R f = 0.52 (100:1 n-hexane/etoac); 1 H NMR (400 MHz, CDCl 3 ) δ 7.29 (d, J = 0.6 Hz, 2H), 2.27 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , 20.17; HRMS (ESI) ([M+H] + ) calcd. for C 7 H 5 Br 2 N 3, , found General Procedure for the Rh-Catalyzed Amidation with Azides To a Schlenk tube equipped with a teflon plug valve and stirbar was added chelating group-containing arenes (1, 0.15 mmol), aryl azides (2, 0.15 mmol), [RhCp*Cl 2 ] 2 (3.7 mg, 4 mol %), NaBARF (5.3 mg, 4 mol %) and H 2 O (1 ml) under atmospheric conditions. The reaction mixture was vigorously stirred on a pre-heated oil bath at 110 o C for 24 h. The reaction was cooled to room temperature, diluted with CH 2 Cl 2 (10 ml) and then washed by water (5 ml x 3).The aqueous layer was extracted by CH 2 Cl 2 (5 ml x 3). The solvents were removed under reduced pressure and the crude reaction mixture was purified by chromatography on silica gel (n-hexane/etoac) as an eluent to give the desired product. 11

12 Characterization Data N-(4-nitrophenyl)-2-(pyridin-2-yl)aniline (3a): Yield 99% (43.3 mg), purified by chromatography on silica gel (5:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.23 (5:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.66 (d, J = 4.7 Hz, 1H), 8.11 (d, J = 9.1 Hz, 2H), 7.83 (dd, J = 11.1, 4.5 Hz, 1H), 7.72 (d, J = 8.1 Hz, 1H), 7.67 (d, J = 7.8 Hz, 1H), 7.60 (d, J = 8.2 Hz, 1H), 7.38 (t, J = 7.7 Hz, 1H), 7.28 (dd, J = 7.4, 5.6 Hz, 1H), 7.15 (t, J = 7.6 Hz, 1H), 7.10 (d, J = 9.1 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , ; IR (KBr) v 3450, 3005, 1580, 1500, 1474, 1275, 1260 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 17 H 13 N 3 O 2, , found Ethyl 4-((2-(pyridin-2-yl)phenyl)amino)benzoate (3b): Yield 93% (44.4 mg), purified by chromatography on silica gel (10:1-5:1 Hexanes/EtOAc), orange solid, TLC R f = 0.20 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.65 (d, J = 4.8 Hz, 1H), 7.94 (d, J = 8.6 Hz, 2H), (m, 1H), 7.69 (d, J = 8.1 Hz, 1H), 7.62 (dd, J = 13.1, 8.0 Hz, 2H), 7.33 (t, J = 7.7 Hz, 1H), 7.23 (dd, J = 6.8, 5.5 Hz, 1H), 7.16 (d, J = 8.6 Hz, 2H), 7.05 (t, J = 7.5 Hz, 1H), 4.35 (q, J = 7.1 Hz, 2H), 1.38 (t, J = 7.1 Hz, 3H); 13 C NMR (100 MHz, 12

13 CDCl 3 ) δ , , , , , , , , , , , , , , , , 60.37, 14.41; IR (KBr) v 3248, 3060, 1704, 1586, 1390, 1365, 1022 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 20 H 18 N 2 O 2, , found N-butyl-4-((2-(pyridin-2-yl)phenyl)amino)benzamide (3c): Yield 92% (47.7 mg) (48h), purified by chromatography on silica gel (5:1 Hexanes/EtOAc), orange oil, TLC R f = 0.21 (5:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.65 (d, J = 4.8 Hz, 1H), 7.80 (t, J = 7.8 Hz, 1H), (m, 4H), 7.55 (d, J = 8.2 Hz, 1H), 7.31 (t, J = 7.7 Hz, 1H), (m, 1H), 7.16 (d, J = 8.4 Hz, 2H), 7.02 (t, J = 7.5 Hz, 1H), 6.03 (s, 1H), 3.43 (dd, J = 13.2, 6.7 Hz, 2H), (m, 2H), 1.40 (dq, J = 14.4, 7.3 Hz, 2H), 0.95 (t, J = 7.3 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , 39.65, 31.86, 20.16, 13.79; IR (KBr) v 3284, 2307, 1785, 1586, 1546, 1425, 1281, 1153 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 22 H 23 N 3 O, , found Phenyl(2-((2-(pyridin-2-yl)phenyl)amino)phenyl)methanone (3d): Yield 90% (47.3 mg), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.22 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.88 (d, J = 4.7 Hz, 1H), (m, 3H),

14 7.59 (m, 3H), 7.53 (t, J = 7.3 Hz, 1H), 7.45 (dd, J = 7.7, 4.3 Hz, 4H), (m, 2H), (m, 1H), 7.11 (t, J = 7.5 Hz, 1H), 6.73 (t, J = 7.5 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , , ; IR (KBr) v 3237, 3005, 1637, 1577, 1474, 1316, 1157, 937 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 24 H 18 N 2 O, , found Bromo-N-(2-(pyridin-2-yl)phenyl)aniline (3e): Yield 93% (45.4 mg), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), orange oil, TLC R f = 0.41 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.71 (d, J = 4.2 Hz, 1H), 7.79 (td, J = 7.8, 1.8 Hz, 1H), 7.70 (d, J = 8.1 Hz, 1H), 7.65 (dd, J = 7.8, 1.3 Hz, 1H), (m, 2H), 7.43 (dd, J = 8.2, 1.2 Hz, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), 6.73 (td, J = 8.0, 1.4 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , ; IR (KBr) v 3210, 3060, 1582, 1519, 1224, 1156, 1119, 1044 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 17 H 13 BrN 2, , found Ethyl 3-bromo-4-((2-(pyridin-2-yl)phenyl)amino)benzoate (3f): 14

15 Yield 96% (57.2 mg), purified by chromatography on silica gel (5:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.56 (4:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.71 (d, J = 4.8 Hz, 1H), 8.21 (d, J = 1.9 Hz, 1H), (m, 2H), 7.68 (t, J = 8.5 Hz, 2H), 7.59 (d, J = 8.2 Hz, 1H), 7.36 (dd, J = 11.0, 4.9 Hz, 2H), 7.25 (dd, J = 7.9, 4.4 Hz, 1H), 7.13 (t, J = 7.5 Hz, 1H), 4.33 (q, J = 7.1 Hz, 2H), 1.37 (t, J = 7.1 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , 60.67, 14.37; IR (KBr) v 3210, 3004, 1707, 1608, 1584, 1394, 1109 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 20 H 17 BrN 2 O 2, , found Chloro-2-iodo-N-(2-(pyridin-2-yl)phenyl)aniline (3g): Yield 93% (56.7 mg), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), white solid, TLC R f = 0.50 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.71 (ddd, J = 4.9, 1.8, 0.9 Hz, 1H), (m, 1H), 7.76 (d, J = 2.4 Hz, 1H), 7.72 (d, J = 8.1 Hz, 1H), 7.67 (dd, J = 7.8, 1.5 Hz, 1H), 7.40 (dd, J = 8.3, 1.0 Hz, 1H), (m, 1H), (m, 2H), 7.14 (dd, J = 8.8, 2.4 Hz, 1H), 7.02 (td, J = 7.8, 1.2 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , 89.57; IR (KBr) v 3256, 3059, 1585, 1561, 1475, 1419, 1380, 1100 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 17 H 12 ClIN 2, , found ,4-Diiodo-N-(2-(pyridin-2-yl)phenyl)aniline (3h): 15

16 Yield 87% (65.0 mg), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), black solid, TLC R f = 0.56 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.71 (d, J = 4.8 Hz, 1H), 8.05 (d, J = 2.0 Hz, 1H), 7.80 (td, J = 7.8, 1.8 Hz, 1H), 7.71 (d, J = 8.1 Hz, 1H), 7.66 (dd, J = 7.8, 1.3 Hz, 1H), (m, 2H), (td, J = 7.8,1.4 Hz, 1H), (m, 1H), 7.09 (d, J = 8.7 Hz, 1H), (td, J = 7.8,0.9 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , 90.45, 81.77; IR (KBr) v 3277, 3057, 1654, 1584, 1546, 1419, 1263, 1079 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 17 H 12 I 2 N 2, , found ,6-Dibromo-4-methyl-N-(2-(pyridin-2-yl)phenyl)aniline (3i): Yield 91% (57.1 mg) (48h), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), white solid, TLC R f = 0.36 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.64 (dt, J = 4.9, 1.4 Hz, 1H), (m, 2H), 7.67 (dd, J = 7.8, 1.4 Hz, 1H), 7.45 (s, 2H), (m, 2H), (m, 1H), 6.45 (d, J = 8.2 Hz, 1H), 2.34 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , 20.31; IR (KBr) v 3208, 3059, 1583, 1537, 1447, 1381, 1287, 1188 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 18 H 14 Br 2 N 2, , found

17 1-((2-(Pyridin-2-yl)phenyl)amino)anthracene-9,10-dione (3j): Yield 98% (55.3 mg), purified by chromatography on silica gel (dichloromethane), red solid, TLC R f = 0.6 (dichloromethane); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.84 (ddd, J = 4.9, 1.7, 0.9 Hz, 1H), 8.36 (dd, J = 7.7, 1.0 Hz, 1H), 8.24 (dd, J = 7.6, 1.1 Hz, 1H), 7.78 (td, J = 7.5, 1.5 Hz, 1H), (m, 4H), (m, 2H), 7.50 (dd, J = 8.7, 1.1 Hz, 1H), (m, 2H), 7.28 (td, J = 7.6, 1.2 Hz, 1H), 7.21 (ddd, J = 7.5, 4.9, 1.1 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , , , , , ; IR (KBr) v 3216, 3063, 1735, 1635, 1584, 1426, 1354, 1174 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 25 H 16 N 2 O 2, , found N-phenyl-2-(pyridin-2-yl)aniline (3k): Yield 90% (33.3 mg) (48h), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.45 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), (d, J = 4.9 Hz, 1H), (m, 1H), 7.72 (d, J = 8.1 Hz, 1H), 7.63 (dd, J = 7.8, 1.4 Hz, 1H), 7.50 (d, J = 8.3 Hz, 1H), 7.29 (td, J = 8.0, 1.5 Hz, 3H), (m, 3H), (m, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , ; IR (KBr) v 3446, 3046, 1587, 17

18 1579, 1449, 1417, 1318, 1278, 694 cm -1 ; HRMS (ESI) ([M+H] + ) calcd.for C 17 H 14 N 2, , found N-(4-methoxyphenyl)-2-(pyridin-2-yl)aniline (3l): Yield 33% (13.7 mg), purified by chromatography on silica gel (15:1 Hexanes/EtOAc), brown solid, TLC R f = 0.41 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.62 (ddd, J = 4.9, 1.7, 0.9 Hz, 1H), (m, 2H), 7.61 (d, J = 7.8 Hz, 1H), (m, 5H), (m, 3H), 3.81 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , IR (KBr) v 3260, 2836, 1587, 1560, 1474, 1263, 1038 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 18 H 16 N 2 O, , found N-(2-(pyridin-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (3m): Yield 38% (18.4 mg), purified by chromatography on silica gel (20:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.59 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.68 (d, J = 4.8 Hz, 1H), 7.83 (t, J = 7.7 Hz, 1H), 7.76 (d, J = 8.1 Hz, 1H), 7.66 (d, J = 7.8 Hz, 1H), (m, 5H), 7.44 (t, J = 7.6 Hz, 18

19 2H), (m, 5H), 6.99 (t, J = 7.5 Hz, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , ; IR (KBr) v 3473, 2919, 1631, 1586, 1523, 1475, 1438, 1324 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 23 H 18 N 2, , found Methoxy-N-(2-(pyridin-2-yl)phenyl)-[1,1'-biphenyl]-2-amine (3n): Yield 81% (42.8 mg) (48h), purified by chromatography on silica gel (10:1Hexanes/EtOAc), orange oil, TLC R f = 0.32 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.08 (d, J = 4.8 Hz, 1H), (m, 1H), 7.62 (d, J = 8.1 Hz, 1H), 7.54 (dd, J = 7.8, 1.4 Hz, 1H), (m, 2H), (m, 5H), (m, 1H), 7.05 (ddd, J = 7.1, 4.9, 1.0 Hz, 1H), 6.90 (d, J = 2.9 Hz, 1H), 6.87 (dd, J = 8.7, 3.0 Hz, 1H), (m, 1H), 3.83 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , , 55.65; IR (KBr) v 3232, 3056, 1586, 1475, 1420, 1269, 1093, 1018 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 24 H 20 N 2 O, , found Bromo-4-methoxy-N-(2-(pyridin-2-yl)phenyl)aniline (3o): 19

20 Yield 91% (48.5 mg), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.48 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.67 (d, J = 4.6 Hz, 1H), 7.78 (t, J = 7.7 Hz, 1H), 7.73 (d, J = 8.0 Hz, 1H), 7.65 (d, J = 7.8 Hz, 1H), 7.35 (d, J = 8.9 Hz, 1H), (m, 3H), 7.17 (d, J = 2.7 Hz, 1H), 6.92 (dt, J = 8.0, 4.1 Hz, 1H), 6.81 (dd, J = 8.9, 2.7 Hz, 1H), 3.78 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 55.81; IR (KBr) v 3440, 2849, 1585, 1513, 1441, 1207, 1028 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 18 H 15 BrN 2 O, , found Methyl-N-(2-(pyridin-2-yl)phenyl)aniline (3p): Yield 91% (35.5 mg), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.48 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.64 (dd, J = 4.1, 0.8 Hz, 1H), (m, 1H), 7.75 (d, J = 8.0 Hz, 1H), 7.66 (dd, J = 7.8, 1.2 Hz, 1H), 7.40 (d, J = 8.0 Hz, 1H), 7.35 (d, J = 8.3 Hz, 1H), (m, 3H), 7.15 (t, J = 7.7 Hz, 1H), 6.93 (t, J = 7.5 Hz, 2H), 2.39 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 18.30; IR (KBr) v 3250, 3052, 1676, 1586, 1560, 1420, 1379, 1241, 1093 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 18 H 16 N 2, , found

21 2-Ethyl-N-(2-(pyridin-2-yl)phenyl)aniline (3q): Yield 88% (36.2 mg), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), orange oil, TLC R f = 0.4 (5:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.63 (d, J = 4.9 Hz, 1H), (m, 2H), 7.66 (dd, J = 7.8, 1.5 Hz, 1H), 7.41 (dd, J = 8.0, 1.1 Hz, 1H), 7.33 (dd, J = 8.3, 1.1 Hz, 1H), (m, 2H), (m, 1H), 7.16 (td, J = 7.8, 1.6 Hz, 1H), 6.99 (td, J = 7.4, 1.2 Hz, 1H), (m, 1H), 2.79 (q, J = 7.5 Hz, 2H), 1.32 (t, J = 7.5 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 24.89, 14.30; IR (KBr) v 3248, 3060, 2963, 1585, 1455, 1266, 1093 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 19 H 18 N 2, , found (Tert-butyl)-N-(2-(pyridin-2-yl)phenyl)aniline (3r): Yield 92% (41.7 mg), purified by chromatography on silica gel (5:1 Hexanes/DCM), orange oil, TLC R f = 0.4 (5:1 Hexanes/DCM); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.56 (d, J = 4.8 Hz, 1H), (m, 2H), 7.68 (dd, J = 7.9, 1.5 Hz, 1H), 7.47 (dd, J = 7.9, 1.5 Hz, 1H), 7.34 (dd, J = 7.9, 1.4 Hz, 1H), (m, 3H), 21

22 (m, 2H), (m, 1H), 1.53 (s, 9H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 34.85, 30.29; IR (KBr) v 3269, 3060, 1607, 1580, 1393, 1197, 935 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 21 H 22 N 2, , found N-(2-(pyridin-2-yl)phenyl)-[1,1'-biphenyl]-2-amine (3s): Yield 96% (46.4 mg), purified by chromatography on silica gel (15:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.50 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 7.95 (d, J = 4.8 Hz, 1H), 7.66 (m, 3H), (m, 6H), 7.42 (dd, J = 9.4, 4.4 Hz, 1H), (m, 3H), (m, 1H), 6.97 (t, J = 7.4 Hz, 1H), 6.92 (t, J = 7.5 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , ; IR (KBr) v 3238, 3028, 1748, 1586, 1558, 1477, 1422, 1112, 1076 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 23 H 18 N 2, , found Methoxy-N-(2-(pyridin-2-yl)phenyl)aniline (3t): Yield 90% (37.3 mg), purified by chromatography on silica gel (5:1 Hexanes/EtOAc), orange solid, TLC R f = 0.20 (5:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.70 (d, J = 4.1 Hz, 1H), 7.79 (td, J = 7.8, 1.8 Hz, 1H), 7.70 (d, J =

23 Hz, 1H), 7.62 (dd, J = 7.8, 1.4 Hz, 1H), 7.57 (d, J = 7.9 Hz, 1H), 7.43 (dd, J = 6.1, 3.2 Hz, 1H), (m, 1H), 7.23 (ddd, J = 7.3, 4.9, 0.9 Hz, 1H), (td, J = 7.5, 0.9 Hz, 1H), (m, 3H), 3.95 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 55.86; IR (KBr) v 3265, 3005, 1587, 1560, 1461, 1263, 1046 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 18 H 16 N 2 O, , found N-(2-(pyridin-2-yl)phenyl)naphthalen-1-amine (3u): Yield 92% (40.9 mg) (48h), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), brown solid, TLC R f = 0.30 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.68 (d, J = 4.7 Hz, 1H), 8.31 (d, J = 8.6 Hz, 1H), (m, 1H), 7.81 (d, J = 3.5 Hz, 2H), 7.72 (d, J = 7.7 Hz, 1H), (m, 4H), (m, 2H), (m, 2H), 6.94 (t, J = 7.4 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , ; IR (KBr) v 3240, 1719, 1579, 1504, 1220, 1123, 1057 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 21 H 16 N 2, , found N-(2-bromophenyl)-4-methyl-2-(pyridin-2-yl)aniline (4a): 23

24 Yield 99% (50.4 mg), purified by chromatography on silica gel (20:1 Hexanes/EtOAc), brown solid, TLC R f = 0.67 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.71 (dd, J = 4.9, 0.8 Hz, 1H), 7.76 (td, J = 7.8, 1.8 Hz, 1H), 7.68 (d, J = 8.1 Hz, 1H), 7.53 (dd, J = 7.9, 1.4 Hz, 1H), 7.46 (d, J = 8.4 Hz, 2H), 7.37 (dd, J = 8.2, 1.4 Hz, 1H), 7.21 (ddd, J = 7.4, 4.9, 1.0 Hz, 1H), 7.14 (m, 2H), 6.69 (td, J = 7.9, 1.4 Hz, 1H), 2.40 (s, 3H).; 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 20.79; IR (KBr) v 3226, 3014, 1587, 1564, 1420, 1222, 1021 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 18 H 15 BrN 2, , found Ethyl 4-((2-bromophenyl)amino)-3-(pyridin-2-yl)benzoate (4b): Yield 95% (56.6 mg), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.40 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.68 (d, J = 4.8 Hz, 1H), 8.42 (s, 1H), 7.93 (d, J = 8.7 Hz, 1H), 7.85 (m, 2H), 7.60 (d, J = 7.9 Hz, 1H), 7.47 (d, J = 8.1 Hz, 1H), 7.42 (d, J = 8.7 Hz, 1H), (m, 2H), 6.86 (t, J = 7.6 Hz, 1H), 4.38 (q, J = 7.1 Hz, 2H), 1.41 (t, J = 7.1 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , 60.60, 14.45; IR (KBr) v 3199, 3064, 1707, 1610, 1587, 1455, 1365, 1240, 1111 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 20 H 17 BrN 2 O 2, , found

25 4-((2-Bromophenyl)amino)-3-(pyridin-2-yl)benzaldehyde (4c): Yield 96% (50.9 mg), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.21 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 9.87 (s, 1H), 8.68 (d, J = 4.5 Hz, 1H), 8.25 (d, J = 1.5 Hz, 1H), 7.87 (m, 2H), 7.74 (d, J = 8.6 Hz, 1H), 7.64 (d, J = 7.9 Hz, 1H), 7.49 (d, J = 7.7 Hz, 1H), 7.42 (d, J = 8.6 Hz, 1H), 7.28 (dd, J = 12.2, 5.5 Hz, 2H), 6.94 (t, J = 7.3 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , ; IR (KBr) v 3222, 3061, 1682, 1574, 1455, 1134, 1045 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 18 H 13 BrN 2 O, , found ((2-Bromophenyl)amino)-3-(pyridin-2-yl)phenyl (4d): 4-methylbenzenesulfonate Yield 90% (66.9 mg), purified by chromatography on silica gel (5:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.68 (2:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.68 (d, J = 4.3 Hz, 1H), 7.77 (m, 3H), 7.54 (dd, J = 7.9, 1.1 Hz, 1H), 7.48 (d, J = 8.1 Hz, 1H), (m, 5H), 7.25 (dd, J = 7.1, 4.8 Hz, 1H), 7.15 (t, J = 7.7 Hz, 1H), 6.81 (dd, J = 9.0, 2.7 Hz, 1H), 6.75 (t, J = 7.6 Hz, 1H), 2.45 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , 21.67; IR (KBr) v 3481, 3005, 1586, 1475, 1455, 1318, 25

26 1092 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 24 H 19 BrN 2 O 3 S, , found ((2-Bromophenyl)amino)-3-(pyridin-2-yl)phenyl (4e): trifluoromethanesulfonate Yield 95% (67.4 mg) (48h), purified by chromatography on silica gel (3:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.29 (3:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.72 (d, J = 4.2 Hz, 1H), 7.85 (td, J = 7.9, 1.5 Hz, 1H), 7.69 (d, J = 8.1 Hz, 1H), 7.58 (dd, J = 8.0, 1.4 Hz, 1H), 7.55 (d, J = 2.9 Hz, 1H), 7.48 (d, J = 9.1 Hz, 1H), 7.40 (dd, J = 8.2, 1.3 Hz, 1H), 7.30 (dd, J = 7.0, 5.2 Hz, 1H), (m, 2H), 6.82 (td, J = 8.0, 1.4 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , ; IR (KBr) v 3454, 1871, 1785, 1585, 1561, 1443, 1321, 1096 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 18 H 12 BrF 3 N 2 O 3 S, , found N-(2-bromophenyl)-4-((tert-butyldimethylsilyl)oxy)-2-(pyridin-2-yl)aniline (4f): Yield 96% (65.6 mg)(48h), purified by chromatography on silica gel (20:1 Hexanes/EtOAc) yellow solid, TLC R f = 0.70 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ 9.91 (s, 1H), 8.70 (d, J = 4.8 Hz, 1H), 7.77 (t, J = 7.7 Hz, 1H), 7.60 (d, 26

27 J = 8.0 Hz, 1H), 7.48 (d, J = 7.9 Hz, 1H), 7.41 (d, J = 8.8 Hz, 1H), (m, 2H), 7.10 (m, 2H), 6.85 (dd, J = 8.8, 2.7 Hz, 1H), 6.63 (t, J = 7.6 Hz, 1H), 1.02 (s, 9H), 0.23 (s, 6H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 25.74, 18.21, -4.36; IR (KBr) v 3248, 2885, 1587, 1563, 1515, 1440, 1361, 1286, 1021 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 23 H 27 BrN 2 OSi, , found N-(2-bromophenyl)-3-methyl-2-(pyridin-2-yl)aniline (4g): Yield 98% (49.9 mg), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), brown oil, TLC R f = 0.46 (10:1 Hexanes/EtOAc). 1 H NMR (400 MHz, CDCl 3 ) δ (d,j = 4.9 Hz 1H), 7.76 (td, J = 7.7, 1.8 Hz, 1H), 7.42 (dd, J = 7.9, 1.4 Hz, 1H), 7.34 (m, 2H), (m, 3H), 7.17 (s, 1H), (m, 1H), 6.98 (d, J = 7.4 Hz, 1H), 6.65 (td, J = 7.9, 1.5 Hz, 1H), 2.22 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 20.67; IR (KBr) v 3350, 3061, 1654, 1579, 1430, 1379, 1121, 1093 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 18 H 15 BrN 2, , found N-(2-bromophenyl)-3-(pyridin-2-yl)naphthalen-2-amine (4h) Yield 98% (55.2 mg), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), orange solid, TLC R f = 0.40 (10:1 Hexanes/EtOAc); 1 H NMR (400 27

28 MHz, CDCl 3 ) δ (s, 1H), 8.76 (d, J = 4.8 Hz, 1H), 8.10 (s, 1H), 7.83 (m, 4H), 7.67 (d, J = 8.2 Hz, 1H), (m, 2H), 7.45 (t, J = 7.3 Hz, 1H), 7.34 (t, J = 7.4 Hz, 1H), 7.30 (dd, J = 8.7, 4.7 Hz, 1H), 7.20 (t, J = 7.7 Hz, 1H), 6.76 (t, J = 7.6 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , ; IR (KBr) v 3225, 3005, 1632, 1584, 1487, 1433, 1022 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 21 H 15 BrN 2, , found Bromo-N-(2-(5-methylpyridin-2-yl)phenyl)aniline (4i): Yield 94% (47.8 mg), purified by chromatography on silica gel (15:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.56 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.54 (s, 1H), (m, 3H), (m, 2H), 7.42 (d, J = 8.1 Hz, 1H), 7.29 (t, J = 8.0 Hz, 1H), 7.14 (t, J = 7.4 Hz, 1H), 7.01 (t, J = 7.5 Hz, 1H), 6.71 (t, J = 7.6 Hz, 1H), 2.38 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 18.16; IR (KBr) v 3223, 3020, 1582, 1560, 1426, 1283,1043 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 18 H 15 BrN 2, , found N-(2-bromophenyl)-3-methoxy-2-(5-methylpyridin-2-yl)aniline (4j): 28

29 Yield 96% (53.2 mg), Purified by chromatography on silica gel (10:1 Hexanes/EtOAc), yellow oil, TLC R f = 0.30 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ 8.98 (s, 1H), 8.58 (s, 1H), 7.54 (d, J = 1.3 Hz, 2H), 7.46 (dd, J = 7.9, 1.4 Hz, 1H), 7.33 (dd, J = 8.2, 1.3 Hz, 1H), (m, 1H), (m, 2H), (m, 2H), 3.80 (s, 3H), 2.37 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 55.79, 18.29; IR (KBr) v 3284, 3002, 1581, 1518, 1447, 1373, 1183 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 19 H 17 BrN 2 O, , found N-(2-bromophenyl)-2-(5-fluoropyridin-2-yl)-4-methylaniline (4k): Yield 98% (52.5 mg), purified by chromatography on silica gel (20:1 Hexanes/EtOAc), brown solid, TLC R f = 0.68 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ 9.77 (s, 1H), 8.56 (d, J = 2.9 Hz, 1H), 7.67 (dd, J = 8.8, 4.3 Hz, 1H), 7.50 (m, 2H), 7.41 (m, 2H), 7.31 (dd, J = 8.2, 1.1 Hz, 1H), (m, 2H), 6.68 (td, J = 7.9, 1.4 Hz, 1H), 2.38 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ (d, J = 254.4), (d, J = 4.1 Hz), , , (d, J = 23.9Hz), , , , , , , (d, J = 18.5 Hz), (d, J = 4.2 Hz),120.45, , , , 20.80; IR (KBr) v 3259, 1588, 1404, 1382, 1142, 1044, 907 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 18 H 14 BrFN 2, , found N-(4-nitrophenyl)-2-(pyrimidin-2-yl)aniline (4l): 29

30 Yield 93% (40.8 mg), purified by chromatography on silica gel (15:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.31 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.85 (d, J = 4.9 Hz, 2H), 8.53 (dd, J = 8.0, 1.4 Hz, 1H), 8.15 (d, J = 9.1 Hz, 2H), 7.59 (d, J = 8.2 Hz, 1H), (m, 1H), (m, 3H), 7.14 (t, J = 7.6 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , ; IR (KBr) v 3288, 3005, 1629, 1577, 1483, 1365, 1185, 1111 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 16 H 12 N 4 O 2, , found (E)-1-(2-((2-bromophenyl)amino)phenyl)ethan-1-one O-methyl oxime (4m): Yield 90% (43.1 mg) (48h), purified by chromatography on silica gel (30:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.45 ( 20:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ 9.37 (s, 1H), 7.57 (d, J = 8.0 Hz, 1H), (m, 3H), (m, 2H), 6.94 (t, J = 7.5 Hz, 1H), 6.79 (t, J = 7.6 Hz, 1H), 4.09 (s, 3H), 2.30 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , 62.45, 13.92; IR (KBr) v 3274, 2816, 1602, 1583, 1478, 1186, 1075 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 15 H 15 BrN 2 O, , found

31 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(2-((2 bromophenyl)amino)phenyl)-9h-purin-9-yl)tetrahydrofuran-3,4-diyl (4n): diacetate Yield 68% (63.7 mg) (48 h), purified by chromatography on silica gel (3:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.58 (1:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ 9.05 (s, 1H), 8.84 (dd, J = 8.0, 1.4 Hz, 1H), 8.30 (s, 1H), 7.57 (dd, J = 8.0, 1.4 Hz, 1H), 7.51 (d, J = 8.3 Hz, 1H), 7.44 (dd, J = 8.2, 1.3 Hz, 1H), (m, 1H), 7.17 (t, J = 7.7 Hz, 1H), 7.09 (t, J = 7.6 Hz, 1H), 6.78 (td, J = 8.0, 1.4 Hz, 1H), 6.31 (d, J = 5.4 Hz, 1H), 6.01 (t, J = 5.5 Hz, 1H), 5.70 (t, J = 5.2 Hz, 1H), (m, 3H), 2.16 (s, 3H), 2.14 (s, 3H), 2.08 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , 86.33, 80.45, 73.07, 70.67, 63.06, 20.75, 20.52, 20.36; IR (KBr) v 1750, 1584, 1520, 1434, 1371, 1312, 1096, 1023 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 28 H 26 BrN 5 O 7, , found General Procedure for the diamination To a Schlenk tube equipped with a teflon plug valve and stirbar was added the monosubstituted product 3 (0.1 mmol), Ar 2 N 3 (0.12 mmol), [RhCp*Cl 2 ] 2 (2.5 mg, 4 31

32 mol %), NaBARF (3.5 mg, 4 mol %) and H 2 O (1 ml) under atmospheric conditions. The reaction mixture was vigorously stirred on a pre-heated oil bath at 110 o C for 48 h. The reaction was cooled to room temperature, diluted with CH 2 Cl 2 (10 ml) and then washed by water (5 ml x 3).The aqueous layer was extracted by CH 2 Cl 2 (5 ml x 3). The solvents were removed under reduced pressure and the crude reaction mixture was purified by silica gel column chromatography (n-hexane/etoac) as an eluent to give the disubstituted product 5. N1,N3-bis(2-bromophenyl)-2-(pyridin-2-yl)benzene-1,3-diamine (5a): Yield 90% (44.6 mg)(48h), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), brown solid, TLC R f = 0.29 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ 8.77 (d, J = 4.8 Hz, 1H), 7.67 (t, J = 7.7 Hz, 1H), 7.52 (d, J = 7.9 Hz, 1H), 7.45 (d, J = 7.9 Hz, 2H), (m, 10H), 6.68 (t, J = 7.6 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , ; IR (KBr) v 3440, 3005, 1641, 1454, 1275, 1260, 1032, 1016 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 23 H 17 Br 2 N 3, , found N1-(2-bromophenyl)-N3-(2-methoxyphenyl)-2-(pyridin-2-yl)benzene-1,3-diamine (5b): Yield 96% (42.8 mg)(48h), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), brown solid, TLC R f = 0.38 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ 8.77 (d, J = 4.7 Hz, 1H), 7.67 (t, J = 7.7 Hz, 1H), 7.53 (d, J = 7.9 Hz, 1H), 7.43 (d, J = 7.9 Hz, 1H), (m, 6H), 7.11 (t, J = 7.7 Hz, 1H), 7.05 (d, J 32

33 = 7.8 Hz, 1H), (m, 4H), 6.66 (t, J = 7.6 Hz, 1H), 3.79 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , , , , 55.68; IR (KBr) v 3500, 3005, 1643, 1577, 1505, 1474, 1428, 1275, 1016 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 24 H 20 BrN 3 O, , found Ethyl 4-((3-((2-bromophenyl)amino)-2-(pyridin-2-yl)phenyl)amino)benzoate (5c): Yield 96% (46.9 mg)(48h), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), brown solid, TLC R f = 0.40 (4:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ 8.75 (d, J = 4.7 Hz, 1H), 7.89 (d, J = 8.5 Hz, 2H), 7.67 (t, J = 7.7 Hz, 1H), 7.47 (dd, J = 12.4, 7.9 Hz, 2H), (m, 7H), 7.04 (s, 1H), 6.96 (d, J = 8.5 Hz, 2H), 6.69 (t, J = 7.6 Hz, 1H), 4.33 (q, J = 7.1 Hz, 2H), 1.37 (t, J = 7.1 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , , , 60.41, 14.41; IR (KBr) v 3346, 3052, 1703, 1605, 1574, 1392, 1212, 1049 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 26 H 22 BrN 3 O 2, , found N1-(2-bromophenyl)-N3-(4-nitrophenyl)-2-(pyridin-2-yl)benzene-1,3-diamine (5d): Yield 72% (33.2 mg) (48h), purified by chromatography on silica gel (4:1 Hexanes/EtOAc), yellow solid, TLC R f = 0.20 (4:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ 8.72 (d, J = 4.7 Hz, 1H), 8.06 (d, J = 9.1 Hz, 2H), 7.70 (t, J = 7.7 Hz, 33

34 1H), 7.54 (s, 1H), 7.47 (t, J = 7.5 Hz, 2H), 7.33 (t, J = 8.1 Hz, 1H), (m, 3H), 7.14 (m, 2H), 7.05 (s, 1H), 6.90 (d, J = 9.1 Hz, 2H), 6.71 (t, J = 7.6 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , ; IR (KBr) v 3373, 3356, 1579, 1501, 1477, 1430, 1306, 1181 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 23 H 17 BrN 4 O 2, , found Ethyl 3-bromo-4-((3-((2-bromophenyl)amino)-2-(pyridin-2-yl)phenyl)amino) benzoate (5e): Yield 92% (44.9 mg)(48h), purified by chromatography on silica gel (10:1 Hexanes/EtOAc), brown solid, TLC R f = 0.50 (4:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ 8.77 (d, J = 4.5 Hz, 1H), 8.12 (d, J = 1.8 Hz, 1H), 7.78 (dd, J = 8.7, 1.7 Hz, 1H), 7.67 (t, J = 7.2 Hz, 1H), 7.60 (s, 1H), 7.47 (d, J = 4.6 Hz, 1H), 7.46 (d, J = 3.9 Hz, 1H), 7.33 (t, J = 8.1 Hz, 1H), (m, 7H), 6.71 (t, J = 7.1 Hz, 1H), 4.32 (q, J = 7.1 Hz, 2H), 1.36 (t, J = 7.1 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , , , , , 60.71, 14.36; IR (KBr) v 3387, 3061, 1708, 1580, 1471, 1408, 1172, 1037 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 26 H 21 Br 2 N 3 O 2, , found N1-(2-bromophenyl)-N3-(4-chloro-2-iodophenyl)-2-(pyridin-2-yl)benzene-1,3-dia mine (5f): 34

35 Yield 96% (55.4 mg)(48h), purified by chromatography on silica gel (20:1 Hexanes/EtOAc), brown solid, TLC R f = 0.48 (10:1 Hexanes/EtOAc); 1 H NMR (400 MHz, CDCl 3 ) δ 8.78 (d, J = 4.7 Hz, 1H), (m, 2H), 7.51 (d, J = 7.9 Hz, 1H), 7.46 (d, J = 7.9 Hz, 1H), (m, 3H), (m, 6H), 7.01 (d, J = 8.0 Hz, 1H), 6.70 (t, J = 7.6 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , , 88.17; IR (KBr) v 3383, 3061, 1579, 1494, 1575, 1400, 1377, 1022 cm -1 ; HRMS (ESI) ([M+H] + ) calcd. for C 23 H 16 BrClIN 3, , found One-pot Cascade Diamination Reaction (Scheme 4) To a Schlenk tube equipped with a teflon plug valve and stirbar was added 2-phenylpyridine (15.5 mg, 0.1 mmol), 1-azido-2-bromobenzene (19.8 mg, 0.1 mmol), [RhCp*Cl 2 ] 2 (2.5 mg, 4 mol %), NaBARF (3.5 mg, 4 mol%) and H 2 O (1 ml) under atmospheric conditions. The reaction mixture was vigorously stirred on a pre-heated oil bath at 110 o C for 24 h and then added [RhCp*Cl 2 ] 2 (2.5 mg, 4 mol %), NaBARF (3.5 mg, 4 mol%) and 1-azido-2-methoxybenzene (23.8 mg, 0.12 mmol) to the reaction mixture and continued stirring for additional 48 h. Then the reaction was cooled to room temperature, diluted with CH 2 Cl 2 (10 ml) and then washed by water (5 ml x 3).The aqueous layer was extracted by CH 2 Cl 2 (5 ml x 3). The solvents were removed under reduced pressure and the crude reaction mixture was purified by silica gel chromatography using (n-hexane/etoac) as an eluent to get the disubstituted product 5a (32.2 mg). 35

36 Schemes S1-S4 To a Schlenk tube equipped with a teflon plug valve and stirbar was added 2-phenylpyridine (15.5 mg, 0.1 mmol), arylazide (19.1 mg, 0.1 mmol), [RhCp*Cl 2 ] 2 (2.5 mg, 4 mol %), NaBARF (3.5 mg, 4 mol%), 3a or 3l (40 mol %) and water (1 ml) under atmospheric conditions. The reaction mixture was vigorously stirred on a pre-heated oil bath at 110 o C for 24 h. The reaction was cooled to room temperature, extracted with CH 2 Cl 2 (10 ml). The solvents were removed under reduced pressure and the crude reaction mixture was purified by silica gel column chromatography (n-hexane/etoac) as an eluent to get the desired product 3b (62%, 19.7 mg). To a Schlenk tube equipped with a teflon plug valve and stirbar was added 2-phenylpyridine (15.5 mg, 0.1 mmol), 1-azido-4-nitrobenzene (16.4 mg, 0.1 mmol), 1-azido-2-methoxybenzene (14.9 mg, 0.1 mmol), [RhCp*Cl 2 ] 2 (2.5 mg, 4 mol %), NaBARF (3.5 mg, 4 mol%), and water (1 ml) under atmospheric conditions. The reaction mixture was vigorously stirred on a pre-heated oil bath at 110 o C for 24 h. The reaction was cooled to room temperature, extracted with CH 2 Cl 2 (10 ml). The solvents were removed under reduced pressure and the crude reaction mixture was 36

37 purified by silica gel column chromatography (n-hexane/etoac) as an eluent to get the desired products 3a and 3t. To a Schlenk tube equipped with a teflon plug valve and stirbar was added 2-phenylpyridine (15.5 mg, 0.1 mmol), 1-azido-4-nitrobenzene (16.4 mg, 0.1 mmol), 1-azido-4-methoxybenzene (14.9 mg, 0.1 mmol), [RhCp*Cl 2 ] 2 (2.5 mg, 4 mol %), NaBARF (3.5 mg, 4 mol%), and water (1 ml) under atmospheric conditions. The reaction mixture was vigorously stirred on a pre-heated oil bath at 110 o C for 24 h. The reaction was cooled to room temperature, extracted with CH 2 Cl 2 (10 ml). The solvents were removed under reduced pressure and the crude reaction mixture was purified by silica gel column chromatography (n-hexane/etoac) as an eluent to get the desired products 3a and 3l. Preliminary Mechanistic Study (Scheme 5 and Scheme S5) On Water: A mixture of [RhCp*Cl 2 ] 2 (123.6 mg, 0.2 mmol), 2-phenylpyridine (124.2 mg, 0.8 mmol ) and H 2 O (5 ml) were stirred at 110 o C for 6 h. The mixture was extracted with dichloromethane (5 ml x 3) and organic layer then filtered through a plug of celite washing with dichloromethane (5 ml x 3). The solvents were removed under reduced pressure and then washed with hexane (10 ml x 5). A cyclometalated compound (6) was obtained as a red-orange solid (169.4 mg, 99%). In DCE: [4] A mixture of [RhCp*Cl 2 ] 2 (123.6 mg, 0.2 mmol ), 2-phenylpyridine (124.2 mg, 0.8 mmol ) in 1,2-dichloroethane (5 ml)were stirred at 110 o C for 6 h. The mixture was filtered through a plug of celite washing with dichloromethane (5 ml x 3). The solvents were removed under reduced 37

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone

More information

Supporting Information

Supporting Information Supporting Information Synthesis of H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis Qiang Wang and Xingwei Li* Dalian Institute of Chemical Physics, Chinese Academy

More information

Supporting Information

Supporting Information Supporting Information Silver-Mediated Oxidative Trifluoromethylation of Alcohols to Alkyl Trifluoromethyl Ethers Jian-Bo Liu, Xiu-Hua Xu, and Feng-Ling Qing Table of Contents 1. General Information --------------------------------------------------------------------------2

More information

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi

More information

Supporting Information. Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template

Supporting Information. Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template Supporting Information Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template Hua-Jin Xu, Yi Lu, *, Marcus E. Farmer, Huai-Wei Wang, Dan Zhao, Yan-Shang Kang, Wei-Yin Sun, *, Jin-Quan Yu

More information

Hualong Ding, Songlin Bai, Ping Lu,* Yanguang Wang*

Hualong Ding, Songlin Bai, Ping Lu,* Yanguang Wang* Supporting Information for Preparation of 2-Amino-3-arylindoles via Pd-Catalyzed Coupling between 3-Diazoindolin-2-imines and Arylboronic Acids as well as Their Extension to 3-Aryl-3-fluoroindolin-2-imines

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic

More information

Supporting Information

Supporting Information Supporting Information (Tetrahedron. Lett.) Cavitands with Inwardly and Outwardly Directed Functional Groups Mao Kanaura a, Kouhei Ito a, Michael P. Schramm b, Dariush Ajami c, and Tetsuo Iwasawa a * a

More information

Suzuki-Miyaura Coupling of Heteroaryl Boronic Acids and Vinyl Chlorides

Suzuki-Miyaura Coupling of Heteroaryl Boronic Acids and Vinyl Chlorides Suzuki-Miyaura Coupling of Heteroaryl Boronic Acids and Vinyl Chlorides Ashish Thakur, Kainan Zhang, Janis Louie* SUPPORTING INFORMATION General Experimental: All reactions were conducted under an atmosphere

More information

hydroxyanthraquinones related to proisocrinins

hydroxyanthraquinones related to proisocrinins Supporting Information for Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins Joyeeta Roy, Tanushree Mal, Supriti Jana and Dipakranjan Mal* Address: Department of Chemistry,

More information

Supporting Information

Supporting Information Supporting Information Divergent Reactivity of gem-difluoro-enolates towards Nitrogen Electrophiles: Unorthodox Nitroso Aldol Reaction for Rapid Synthesis of -Ketoamides Mallu Kesava Reddy, Isai Ramakrishna,

More information

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL

More information

Supporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials

Supporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Supporting Material 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Srinivas Olepu a, Praveen Kumar Suryadevara a, Kasey Rivas b, Christophe L. M. J. Verlinde

More information

Carbonylative Coupling of Allylic Acetates with. Arylboronic Acids

Carbonylative Coupling of Allylic Acetates with. Arylboronic Acids Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Carbonylative Coupling of Allylic Acetates with Arylboronic Acids Wei Ma, a Ting Yu, Dong Xue,*

More information

Supporting Information for

Supporting Information for Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,

More information

SYNTHESIS OF A 3-THIOMANNOSIDE

SYNTHESIS OF A 3-THIOMANNOSIDE Supporting Information SYNTHESIS OF A 3-THIOMANNOSIDE María B Comba, Alejandra G Suárez, Ariel M Sarotti, María I Mangione* and Rolando A Spanevello and Enrique D V Giordano Instituto de Química Rosario,

More information

Supporting Information

Supporting Information Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,

More information

Supplementary Information (Manuscript C005066K)

Supplementary Information (Manuscript C005066K) Supplementary Information (Manuscript C005066K) 1) Experimental procedures and spectroscopic data for compounds 6-12, 16-19 and 21-29 described in the paper are given in the supporting information. 2)

More information

Divergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site of Acid Catalysts

Divergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site of Acid Catalysts Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Divergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site

More information

Supporting Information

Supporting Information Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2012 Subcellular Localization and Activity of Gambogic Acid Gianni Guizzunti,* [b] Ayse Batova, [a] Oraphin Chantarasriwong,

More information

Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A

Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A Fuerst et al. Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A S1 Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers:

More information

Supporting Information. Rhodium(III)-Catalyzed Synthesis of Naphthols via C-H Activation. of Sulfoxonium Ylides. Xingwei Li*, Table of Contents

Supporting Information. Rhodium(III)-Catalyzed Synthesis of Naphthols via C-H Activation. of Sulfoxonium Ylides. Xingwei Li*, Table of Contents Supporting Information Rhodium(III)-Catalyzed Synthesis of Naphthols via C-H Activation of Sulfoxonium Ylides Youwei Xu,, Xifa Yang,, Xukai Zhou,, Lingheng Kong,, and Xingwei Li*, Dalian Institute of Chemical

More information

Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4)

Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4) Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4) A solution of propenyl magnesium bromide in THF (17.5 mmol) under nitrogen atmosphere was cooled in an ice bath and

More information

Pd(II) Catalyzed C3-selective arylation of pyridine with (hetero)arenes SUPPORTING INFORMATION

Pd(II) Catalyzed C3-selective arylation of pyridine with (hetero)arenes SUPPORTING INFORMATION Pd(II) Catalyzed C3-selective arylation of pyridine with (hetero)arenes Guo-Lin Gao,, Wujiong Xia, Pankaj Jain and Jin-Quan Yu *, Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey

More information

Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl. α-iminoesters through Auto-Tandem Catalysis

Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl. α-iminoesters through Auto-Tandem Catalysis Supporting Information Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl α-iminoesters through Auto-Tandem Catalysis Azusa Kondoh, b and Masahiro Terada* a a Department of Chemistry, Graduate School

More information

The First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C

The First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C Supporting Information The First Asymmetric Total Syntheses and Determination of Absolute Configurations of Xestodecalactones B and C Qiren Liang, Jiyong Zhang, Weiguo Quan, Yongquan Sun, Xuegong She*,,

More information

Supporting Information

Supporting Information Supporting Information for Engineering of indole-based tethered biheterocyclic alkaloid meridianin into -carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization

More information

for Brønsted Base-Mediated Aziridination of 2- Alkyl Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-1,4-Dicarbonyl Compounds by Iminoiodanes

for Brønsted Base-Mediated Aziridination of 2- Alkyl Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-1,4-Dicarbonyl Compounds by Iminoiodanes 10.1071/CH16580_AC CSIRO 2017 Australian Journal of Chemistry 2017, 70(4), 430-435 Supplementary Material for Brønsted Base-Mediated Aziridination of 2- Alkyl Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-1,4-Dicarbonyl

More information

Supporting Information. Table of Contents. 1. General Notes Experimental Details 3-12

Supporting Information. Table of Contents. 1. General Notes Experimental Details 3-12 Supporting Information Table of Contents page 1. General Notes 2 2. Experimental Details 3-12 3. NMR Support for Timing of Claisen/Diels-Alder/Claisen 13 4. 1 H and 13 C NMR 14-37 General Notes All reagents

More information

Supporting Information:

Supporting Information: Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2016 Supporting Information: A metal free reduction of aryl-n-nitrosamines to corresponding hydrazines

More information

Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis

Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Kazushi Watanabe, Yuto Suzuki, Kenta Aoki, Akira Sakakura, Kiyotake Suenaga, and Hideo Kigoshi* Department of Chemistry,

More information

Poly(4-vinylimidazolium)s: A Highly Recyclable Organocatalyst Precursor for. Benzoin Condensation Reaction

Poly(4-vinylimidazolium)s: A Highly Recyclable Organocatalyst Precursor for. Benzoin Condensation Reaction Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 24 Supporting Information Poly(4-vinylimidazolium)s: A Highly Recyclable rganocatalyst Precursor

More information

Efficient Pd-Catalyzed Amination of Heteroaryl Halides

Efficient Pd-Catalyzed Amination of Heteroaryl Halides 1 Efficient Pd-Catalyzed Amination of Heteroaryl Halides Mark D. Charles, Philip Schultz, Stephen L. Buchwald* Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139 Supporting

More information

Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles

Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles Supporting Information for Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles Xiao-Li Lian, Zhi-Hui Ren, Yao-Yu

More information

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S Supporting Text Synthesis of (2S,3S)-2,3-bis(3-bromophenoxy)butane (3). Under N 2 atmosphere and at room temperature, a mixture of 3-bromophenol (0.746 g, 4.3 mmol) and Cs 2 C 3 (2.81 g, 8.6 mmol) in DMS

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION Supplementary Method Synthesis of 2-alkyl-MPT(R) General information (R) enantiomer of 2-alkyl (18:1) MPT (hereafter designated as 2-alkyl- MPT(R)), was synthesized as previously described 1, with some

More information

Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy

Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) for Effect of Conjugation and Aromaticity of 3,6 Di-substituted

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2016 Supporting Information Synthesis of Biaryl Sultams Using Visible-Light-Promoted Denitrogenative

More information

Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications This journal is The Royal Society of Chemistry 2012

Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications This journal is The Royal Society of Chemistry 2012 Supporting Information. Experimental Section: Summary scheme H 8 H H H 9 a H C 3 1 C 3 A H H b c C 3 2 3 C 3 H H d e C 3 4 5 C 3 H f g C 2 6 7 C 2 H a C 3 B H c C 3 General experimental details: All solvents

More information

Supporting Information for: Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions

Supporting Information for: Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions Supporting Information for: Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions Patrick S. Fier* and Kevin M. Maloney* S1 General experimental details All reactions

More information

Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline

Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline Chunpu Li 1,2, Lei Zhang 2, Shuangjie Shu 2 and Hong Liu* 1,2 Address: 1 Department of Medicinal

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2012 69451 Weinheim, Germany Concise Syntheses of Insect Pheromones Using Z-Selective Cross Metathesis** Myles B. Herbert, Vanessa M. Marx, Richard L. Pederson, and Robert

More information

Scalable Synthesis of Fmoc-Protected GalNAc-Threonine Amino Acid and T N Antigen via Nickel Catalysis

Scalable Synthesis of Fmoc-Protected GalNAc-Threonine Amino Acid and T N Antigen via Nickel Catalysis Scalable Synthesis of Fmoc-Protected GalNAc-Threonine Amino Acid and T N Antigen via Nickel Catalysis Fei Yu, Matthew S. McConnell, and Hien M. Nguyen* Department of Chemistry, University of Iowa, Iowa

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION Synthetic chemistry ML5 and ML4 were identified as K P.(TREK-) activators using a combination of fluorescence-based thallium flux and automated patch-clamp assays. ML5, ML4, and ML5a were synthesized using

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information Palladium-Catalyzed Oxidative Allylation of Bis[(pinacolato)boryl]methane:

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Pd-Catalyzed C-H Activation/xidative Cyclization of Acetanilide with orbornene:

More information

Supporting Information

Supporting Information Supporting Information Synthesis of 2-Benzazepines from Benzylamines and MBH Adducts Under Rhodium(III) Catalysis via C(sp 2 ) H Functionalization Ashok Kumar Pandey, a Sang Hoon Han, a Neeraj Kumar Mishra,

More information

Supplementary Material

Supplementary Material 10.1071/CH13324_AC CSIRO 2013 Australian Journal of Chemistry 2013, 66(12), 1570-1575 Supplementary Material A Mild and Convenient Synthesis of 1,2,3-Triiodoarenes via Consecutive Iodination/Diazotization/Iodination

More information

Supporting Information. (1S,8aS)-octahydroindolizidin-1-ol.

Supporting Information. (1S,8aS)-octahydroindolizidin-1-ol. SI-1 Supporting Information Non-Racemic Bicyclic Lactam Lactones Via Regio- and cis-diastereocontrolled C H insertion. Asymmetric Synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.

More information

All solvents and reagents were used as obtained. 1H NMR spectra were recorded with a Varian

All solvents and reagents were used as obtained. 1H NMR spectra were recorded with a Varian SUPPLEMETARY OTE Chemistry All solvents and reagents were used as obtained. 1H MR spectra were recorded with a Varian Inova 600 MR spectrometer and referenced to dimethylsulfoxide. Chemical shifts are

More information

Iron Catalyzed Cross Couplings of Azetidines: Application to an Improved Formal Synthesis of a Pharmacologically Active Molecule

Iron Catalyzed Cross Couplings of Azetidines: Application to an Improved Formal Synthesis of a Pharmacologically Active Molecule Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Iron Catalyzed Cross Couplings of Azetidines: Application to an Improved Formal Synthesis of a

More information

Supporting Information

Supporting Information Supporting Information Efficient Benzimidazolidinone Synthesis via Rhodium-Catalyzed Double-Decarbonylative C C Activation/Cycloaddition between Isatins and Isocyanates Rong Zeng, Peng-hao Chen, and Guangbin

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION DOI: 10.1038/NCHEM.1989 Cooperative activation of cyclobutanones and olefins leads to bridged ring systems by a catalytic [4+2] coupling Haye Min Ko and Guangbin Dong* Department of chemistry and biochemistry,

More information

A Facile and General Approach to 3-((Trifluoromethyl)thio)- 4H-chromen-4-one

A Facile and General Approach to 3-((Trifluoromethyl)thio)- 4H-chromen-4-one A Facile and General Approach to 3-((Trifluoromethyl)thio)- 4H-chromen-4-one Haoyue Xiang and Chunhao Yang* State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy

More information

Supporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and

Supporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and Supporting Information for A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3- butyn-2-ols Jie Li and

More information

Supplementary Information

Supplementary Information Electronic Supplementary Material (ESI) for Chemical Communications. This journal is The Royal Society of Chemistry 2017 Supplementary Information Ruthenium(II)-Catalyzed Intermolecular Synthesis of 2-Arylindolines

More information

1. Reagents: All commercial materials were used as received unless otherwise noted. The following solvents were obtained from a JC Meyer solvent dispe

1. Reagents: All commercial materials were used as received unless otherwise noted. The following solvents were obtained from a JC Meyer solvent dispe Supporting Information Pd-catalyzed Mono-selective ortho-c H Alkylation of N-Quinolyl Benzamides: Evidence for Stereo-retentive Coupling of Secondary Alkyl Iodides Shu-Yu Zhang, Qiong Li, Gang He, William

More information

Supporting Information for. An Approach to Tetraphenylenes via Pd-Catalyzed C H Functionalization

Supporting Information for. An Approach to Tetraphenylenes via Pd-Catalyzed C H Functionalization Supporting Information for An Approach to Tetraphenylenes via Pd-Catalyzed C H Functionalization Hang Jiang, Yu Zhang, Dushen Chen, Bo Zhou, and Yanghui Zhang * Department of Chemistry, and Shanghai Key

More information

Supporting Information

Supporting Information Electronic upplementary Material (EI) for rganic Chemistry rontiers. This journal is the Partner rganisations 0 upporting Information Convenient ynthesis of Pentafluoroethyl Thioethers via Catalytic andmeyer

More information

Ruthenium-catalyzed highly regio- and stereoselective hydroarylation of aromatic sulfoxides with alkynes via C-H bond activation

Ruthenium-catalyzed highly regio- and stereoselective hydroarylation of aromatic sulfoxides with alkynes via C-H bond activation Electronic upplementary Material (EI) for ChemComm. This journal is The Royal ociety of Chemistry 2014 Ruthenium-catalyzed highly regio- and stereoselective hydroarylation of aromatic sulfoxides with alkynes

More information

Synthesis of borinic acids and borinate adducts using diisopropylaminoborane

Synthesis of borinic acids and borinate adducts using diisopropylaminoborane Synthesis of borinic acids and borinate adducts using diisopropylaminoborane Ludovic Marciasini, Bastien Cacciuttolo, Michel Vaultier and Mathieu Pucheault* Institut des Sciences Moléculaires, UMR 5255,

More information

SUPPORTING INFORMATION

SUPPORTING INFORMATION SUPPRTING INFRMATIN A Direct, ne-step Synthesis of Condensed Heterocycles: A Palladium-Catalyzed Coupling Approach Farnaz Jafarpour and Mark Lautens* Davenport Chemical Research Laboratories, Chemistry

More information

Efficient Mono- and Bis-Functionalization of 3,6-Dichloropyridazine using (tmp) 2 Zn 2MgCl 2 2LiCl ** Stefan H. Wunderlich and Paul Knochel*

Efficient Mono- and Bis-Functionalization of 3,6-Dichloropyridazine using (tmp) 2 Zn 2MgCl 2 2LiCl ** Stefan H. Wunderlich and Paul Knochel* Efficient Mono- and Bis-Functionalization of 3,6-Dichloropyridazine using (tmp) 2 Zn 2Mg 2 2Li ** Stefan H. Wunderlich and Paul Knochel* Ludwig Maximilians-Universität München, Department Chemie & Biochemie

More information

Supporting Information for Exploration of C H and N H-bond functionalization towards 1-(1,2-diarylindol-3-yl)- tetrahydroisoquinolines

Supporting Information for Exploration of C H and N H-bond functionalization towards 1-(1,2-diarylindol-3-yl)- tetrahydroisoquinolines Supporting Information for Exploration of C H and N H-bond functionalization towards 1-(1,2-diarylindol-3-yl)- tetrahydroisoquinolines Michael Ghobrial, Marko D. Mihovilovic and Michael Schnürch* Address:

More information

Enantioselective Conjugate Addition of 3-Fluoro-Oxindoles to. Vinyl Sulfone: An Organocatalytic Access to Chiral. 3-Fluoro-3-Substituted Oxindoles

Enantioselective Conjugate Addition of 3-Fluoro-Oxindoles to. Vinyl Sulfone: An Organocatalytic Access to Chiral. 3-Fluoro-3-Substituted Oxindoles Enantioselective Conjugate Addition of 3-Fluoro-Oxindoles to Vinyl Sulfone: An Organocatalytic Access to Chiral 3-Fluoro-3-Substituted Oxindoles Xiaowei Dou and Yixin Lu * Department of Chemistry & Medicinal

More information

Indium Triflate-Assisted Nucleophilic Aromatic Substitution Reactions of. Nitrosobezene-Derived Cycloadducts with Alcohols

Indium Triflate-Assisted Nucleophilic Aromatic Substitution Reactions of. Nitrosobezene-Derived Cycloadducts with Alcohols Supporting Information Indium Triflate-Assisted ucleophilic Aromatic Substitution Reactions of itrosobezene-derived Cycloadducts with Alcohols Baiyuan Yang and Marvin J. Miller* Department of Chemistry

More information

Supporting Information for

Supporting Information for Supporting Information for Room Temperature Palladium-Catalyzed Arylation of Indoles icholas R. Deprez, Dipannita Kalyani, Andrew Krause, and Melanie S. Sanford* University of Michigan Department of Chemistry,

More information

Supporting Information

Supporting Information Supporting Information An efficient and general method for the Heck and Buchwald- Hartwig coupling reactions of aryl chlorides Dong-Hwan Lee, Abu Taher, Shahin Hossain and Myung-Jong Jin* Department of

More information

Synthesis of Secondary and Tertiary Amine- Containing MOFs: C-N Bond Cleavage during MOF Synthesis

Synthesis of Secondary and Tertiary Amine- Containing MOFs: C-N Bond Cleavage during MOF Synthesis Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2015 Supporting Information Synthesis of Secondary and Tertiary Amine- Containing MFs: C-N Bond

More information

Highly Regioselective Lithiation of Pyridines Bearing an Oxetane Unit by n-buthyllithium

Highly Regioselective Lithiation of Pyridines Bearing an Oxetane Unit by n-buthyllithium Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Highly Regioselective Lithiation of Pyridines Bearing an Oxetane Unit by n-buthyllithium Guy Rouquet,*

More information

An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters

An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters S1 An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters Chris V. Galliford and Karl A. Scheidt* Department of Chemistry, Northwestern University, 2145 Sheridan

More information

Supporting Information

Supporting Information Supporting Information Organocatalytic Enantioselective Formal Synthesis of Bromopyrrole Alkaloids via Aza-Michael Addition Su-Jeong Lee, Seok-Ho Youn and Chang-Woo Cho* Department of Chemistry, Kyungpook

More information

Supporting Information

Supporting Information Supporting Information ACA: A Family of Fluorescent Probes that Bind and Stain Amyloid Plaques in Human Tissue Willy M. Chang, a Marianna Dakanali, a Christina C. Capule, a Christina J. Sigurdson, b Jerry

More information

Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions

Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions SUPPORTIG IFORMATIO Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions Alexey Volkov, a Fredrik Tinnis, a and Hans Adolfsson.* a a Department of Organic Chemistry,

More information

Supporting Information. Efficient N-arylation and N-alkenylation of the five. DNA/RNA nucleobases

Supporting Information. Efficient N-arylation and N-alkenylation of the five. DNA/RNA nucleobases Supporting Information Efficient -arylation and -alkenylation of the five DA/RA nucleobases Mikkel F. Jacobsen, Martin M. Knudsen and Kurt V. Gothelf* Center for Catalysis and Interdisciplinary anoscience

More information

Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins

Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins S1 Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins Antonia Kouridaki, Tamsyn Montagnon, Maria Tofi and Georgios Vassilikogiannakis* Department of

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Palladium-Catalyzed Regio-selective xidative C-H

More information

Supporting Information

Supporting Information 1 A regiodivergent synthesis of ring A C-prenyl flavones Alberto Minassi, Anna Giana, Abdellah Ech-Chahad and Giovanni Appendino* Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche

More information

Block: Synthesis, Aggregation-Induced Emission, Two-Photon. Absorption, Light Refraction, and Explosive Detection

Block: Synthesis, Aggregation-Induced Emission, Two-Photon. Absorption, Light Refraction, and Explosive Detection Electronic Supplementary Information (ESI) Luminogenic Materials Constructed from Tetraphenylethene Building Block: Synthesis, Aggregation-Induced Emission, Two-Photon Absorption, Light Refraction, and

More information

Supporting Information

Supporting Information Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2014 Supporting Information Palladium-Catalyzed Construction of Spirooxindoles by Arylative Cyclization of 3-( -Disubstituted)allylidene-2-Oxindoles

More information

Experimental details

Experimental details Supporting Information for A scalable synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole ((S)-t-BuPyx) ligand Hideki Shimizu 1,2, Jeffrey C. Holder 1 and Brian M. Stoltz* 1 Address:

More information

SUPPORTING INFORMATION

SUPPORTING INFORMATION UPPRTING INFRMATIN Application of a Rhodium-Catalyzed Addition/Cyclization equence Toward the ynthesis of Polycyclic eteroaromatics Nai-Wen Tseng and Mark Lautens* Davenport Laboratories, Chemistry Department,

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Supporting Information Enantioselective Synthesis of Axially Chiral Vinyl arenes through Palladium-catalyzed

More information

Asymmetric Synthesis of Hydrobenzofuranones via Desymmetrization of Cyclohexadienones using the Intramolecular Stetter Reaction

Asymmetric Synthesis of Hydrobenzofuranones via Desymmetrization of Cyclohexadienones using the Intramolecular Stetter Reaction Asymmetric Synthesis of Hydrobenzofuranones via Desymmetrization of Cyclohexadienones using the Intramolecular Stetter Reaction Qin Liu and Tomislav Rovis* Department of Chemistry, Colorado State University

More information

How to build and race a fast nanocar Synthesis Information

How to build and race a fast nanocar Synthesis Information How to build and race a fast nanocar Synthesis Information Grant Simpson, Victor Garcia-Lopez, Phillip Petemeier, Leonhard Grill*, and James M. Tour*, Department of Physical Chemistry, University of Graz,

More information

Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801.

Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801. Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801. Alan L. Sewell a, Mathew V. J. Villa a, Mhairi Matheson a, William G. Whittingham b, Rodolfo Marquez a*. a) WestCHEM, School of Chemistry,

More information

Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable

Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable 1 Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable immobilized AlCl 3 on γ-al 2 O 3 SUPPLEMETARY DATA Typical Procedure to the preparation of Azides Phenyl azide Phenyl azide was

More information

Supporting Information

Supporting Information Supporting Information An Extremely Active and General Catalyst for Suzuki Coupling Reactions of Unreactive Aryl Chlorides Dong-Hwan Lee and Myung-Jong Jin* School of Chemical Science and Engineering,

More information

Reactions. James C. Anderson,* Rachel H. Munday. School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK

Reactions. James C. Anderson,* Rachel H. Munday. School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK Vinyl-dimethylphenylsilanes as Safety Catch Silanols in Fluoride free Palladium Catalysed Cross Coupling Reactions. James C. Anderson,* Rachel H. Munday School of Chemistry, University of Nottingham, Nottingham,

More information

Supporting Information For:

Supporting Information For: Supporting Information For: Highly Fluorinated Ir(III)- 2,2 :6,2 -Terpyridine -Phenylpyridine-X Complexes via Selective C-F Activation: Robust Photocatalysts for Solar Fuel Generation and Photoredox Catalysis

More information

A General and Mild Copper-Catalyzed Arylation of Diethyl Malonate

A General and Mild Copper-Catalyzed Arylation of Diethyl Malonate A General and Mild Copper-Catalyzed Arylation of Diethyl Malonate 1 Edward J. Hennessy and Stephen L. Buchwald Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139 Supporting

More information

Supporting Information

Supporting Information Supporting Information SmI 2 -Mediated Carbon-Carbon Bond Fragmentation in α-aminomethyl Malonates Qiongfeng Xu,, Bin Cheng, $, Xinshan Ye,*, and Hongbin Zhai*,,,$ The State Key Laboratory of Natural and

More information

Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes

Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,

More information

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003 Supporting Information for Angew. Chem. Int. Ed. Z53001 Wiley-VCH 2003 69451 Weinheim, Germany 1 Ordered Self-Assembly and Electronic Behavior of C 60 -Anthrylphenylacetylene Hybrid ** Seok Ho Kang 1,

More information

Curtius-Like Rearrangement of Iron-Nitrenoid Complex and. Application in Biomimetic Synthesis of Bisindolylmethanes

Curtius-Like Rearrangement of Iron-Nitrenoid Complex and. Application in Biomimetic Synthesis of Bisindolylmethanes Supporting Information Curtius-Like Rearrangement of Iron-itrenoid Complex and Application in Biomimetic Synthesis of Bisindolylmethanes Dashan Li,, Ting Wu,, Kangjiang Liang,, and Chengfeng Xia*,, State

More information

Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3

Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3 S1 Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3 David Bézier, Sehoon Park and Maurice Brookhart* Department of Chemistry, University of North Carolina at Chapel Hill,

More information

Solvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols

Solvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Solvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols

More information

Photochemical Nickel-Catalyzed C-H Arylation: Synthetic Scope and Mechanistic Investigations

Photochemical Nickel-Catalyzed C-H Arylation: Synthetic Scope and Mechanistic Investigations Photochemical Nickel-Catalyzed C-H Arylation: Synthetic Scope and Mechanistic Investigations Drew R. Heitz, John C. Tellis, and Gary A. Molander* Roy and Diana Vagelos Laboratories, Department of Chemistry,

More information

Supporting Information:

Supporting Information: Enantioselective Synthesis of (-)-Codeine and (-)-Morphine Barry M. Trost* and Weiping Tang Department of Chemistry, Stanford University, Stanford, CA 94305-5080 1. Aldehyde 7. Supporting Information:

More information

Parallel sheet structure in cyclopropane γ-peptides stabilized by C-H O hydrogen bonds

Parallel sheet structure in cyclopropane γ-peptides stabilized by C-H O hydrogen bonds Parallel sheet structure in cyclopropane γ-peptides stabilized by C- hydrogen bonds M. Khurram N. Qureshi and Martin D. Smith* Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge

More information