Supporting Information. DBU-Mediated Metal-Free Oxidative Cyanation of α-amino. Carbonyl Compounds: Using Molecular Oxygen as the Oxidant

Size: px
Start display at page:

Download "Supporting Information. DBU-Mediated Metal-Free Oxidative Cyanation of α-amino. Carbonyl Compounds: Using Molecular Oxygen as the Oxidant"

Transcription

1 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information DBU-Mediated Metal-Free Oxidative Cyanation of α-amino Carbonyl Compounds: Using Molecular Oxygen as the Oxidant Lei Li, Qian Wang, Pei Liu, Hua Meng, Xing-Lan Kan, Qun Liu, and Yu-Long Zhao,*, Department of Chemistry, Northeast Normal University, Changchun, , P. R. China Zhejiang Sucon Silicone Co.,Ltd., Shaoxing, , P. R. China Table of contents I. General Information...S2 II. General Procedure for the Preparation of 3...S3-S9 III. General Procedure for the Preparation of 6... S10-S11 IV. Crystal ORTEP drawing of compound 3a...S12 V. Copies of 1 H NMR and 13 C NMR spectra of compounds 3, 4 and 6...S13-S30 S1

2 I. General Information All reagents were commercial and were used without further purification. Chromatography was carried on flash silica gel ( mesh). All reactions were monitored by TLC, which was performed on precoated aluminum sheets of silica gel 60 (F254). Melting points were uncorrected. Unless noted, the 1 H NMR spectra were recorded at 400 MHz and 500 MHz in CDCl 3 and the 13 C NMR spectra were recorded at 125 MHz in CDCl 3 with TMS as internal standard. All coupling constants (J values) were reported in Hertz (Hz). High-resolution mass spectra (HRMS) were obtained using a Bruker microtof II focus spectrometer (ESI). The compound 3a was glued on a glass fiber. Data were collected at 293K using graphite-monochromated Mo Kα radiation (λ = Å) and IP technique in the range 2.19 < θ < Empirical absorption correction was applied. The structures were solved by the direct method and refined by the full-matrix least-squares method on F2 using the SHELXS 97 crystallographic software package. Anisotropic thermal parameters were used to refine all non-hydrogen atoms. Hydrogen atoms were located from difference Fourier maps. S2

3 II. General Procedure for the Preparation of 3 (3a as Example): R O O H N DBU (1.5 equiv) N Ar + TMSCN Ar DMF, rt, 4-10 min CN R To a solution of (E)-4-(4-chlorophenyl)-1-(p-tolylamino)but-3-en-2-one 1a (0.2 mmol, 57.1 mg) and TMSCN 2 (0.30 mmol, ml) in DMF (1.5 ml) was added DBU (0.3 mmol, ml). Then the reaction mixture was stirred at room temperature in open air for 5 min. After 1a was consumed (monitored by TLC), the reaction mixture was poured into water (50 ml) and extracted with CH 2 Cl 2 (10 ml 3). The combined organic extracts were dried over anhydrous Na 2 SO 4, filtered and concentrated under reduced pressure to yield the corresponding crude product, which was purified by chromatography (silica gel, petroleum ether/acetone = 10/1, v/v) to give 3a (44.4 mg, 72%) as a yellow solid. (1E,3E)-4-(4-chlorophenyl)-2-oxo-N-(p-tolyl)but-3-enimidoyl cyanide (3a): Yellow solid; m.p o C; 1 H NMR (CDCl 3, 500 MHz) δ: 7.91 (d, J = 16.0 Hz, 1H), 7.83 (d, J = 16.0 Hz, 1H), 7.63 (d, J = 8.5 Hz, 2H), 7.50 (d, J = 8.5 Hz, 2H), 7.42 (d, J = 8.5 Hz, 2H), 7.35 (d, J = 8.5 Hz, 2H), 2.45 (s, 3H); 13 CNMR (CDCl 3, 125 MHz) δ: 183.5, 145.4, 143.3, 142.2, 137.4, 135.8, 132.8, 130.3, 130.2, 129.4, 123.0, 118.4, 110.6, 21.6; IR (KBr) ν: 2921, 2215, 1618, 1600, 1556, 1445, 1319, 1108, 1060 cm -1 ; HRMS (ESI-TOF)calcd for C 18 H 13 ClN 2 ONa + ([M + Na] + ): , found: (1E,3E)-2-oxo-N-(p-tolyl)-4-(4-(trifluoromethyl)phenyl)but-3-enimidoyl cyanide (3b): S3

4 O N CN F 3 C Yellow solid; m.p o C; 1 H NMR (500 MHz, CDCl 3 ) δ: 7.94 (d, J = 4.0 Hz, 2H), 7.79 (d, J = 8.0 Hz, 2H), 7.69 (d, J = 8.5 Hz, 2H), 7.53 (d, J = 8.0 Hz, 2H), 7.36 (d, J = 8.0 Hz, 2H), 2.46 (s, 3H); 13 C NMR (125 MHz, CDCl 3 ) δ: 183.5, 144.7, 143.2, 142.5, 137.6, 135.4, (q, J = 32.7 Hz), 130.3, 129.1, (q, J = 3.6 Hz), (q, J = Hz), 123.2, 120.2, 110.6, 21.6; IR (KBr) ν: 2926, 2211, 1608, 1607, 1550, 1324, 1117, 1066 cm -1 ; HRMS (ESI-TOF)calcd for C 19 H 14 F 3 N 2 O + ([M + H] + ): , found: (1E,3E)-4-(2-chlorophenyl)-2-oxo-N-(p-tolyl)but-3-enimidoyl cyanide (3c): Yellow solid; m.p o C; 1 H NMR (500 MHz, CDCl 3 ) δ: 8.39 (d, J = 16.0 Hz, 1H), (m, 2H), 7.50 (d, J = 8.5 Hz, 2H), 7.46 (dd, J = 8.0 Hz, 1.0 Hz, 1H), (m, 4H), 2.45 (s, 3H); 13 C NMR (125 MHz, CDCl 3 ) δ: 183.4, 143.2, 142.5, 142.3, 136.2, 135.6, 132.5, 132.0, 130.4, 130.3, 128.0, 127.1, 123.0, 120.3, 110.6, 21.5; IR (KBr) ν: 3032, 2217, 1663, 1595, 1328, 1272, 1208 cm -1 ; HRMS (ESI-TOF)calcd for C 18 H 14 ClN 2 O + ([M + H] + ): , found: (1E,3E)-2-oxo-N,4-dip-tolylbut-3-enimidoyl cyanide (3d): Yellow solid; m.p o C; 1 H NMR (500 MHz, CDCl 3 ) δ: 7.96 (d, J = 16.0 Hz, 1H), 7.81 (d, J = 16.0 Hz, 1H), 7.60 (d, J = 8.0 Hz, 2H), 7.48 (d, J = 8.5 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 7.25 (d, J = 8.5 Hz, 2H), 2.45 (s, 3H), 2.41 (s, 3H); 13 C NMR (125 MHz, CDCl 3 ) δ: 183.6, 147.2, 143.5, S4

5 142.3, 141.8, 136.2, 131.6, 130.2, 129.8, 129.2, 122.8, 116.8, 110.7, 21.7, 21.5; HRMS (ESI-TOF) calcd for C 19 H 17 N 2 O + ([M + H] + ): , found: (1E,3E)-4-(4-methoxyphenyl)-2-oxo-N-p-tolylbut-3-enimidoyl cyanide (3e): O N CN MeO Yellow solid; m.p o C; 1 H NMR (500 MHz, CDCl 3 ) δ: 7.94 (d, J = 16.0 Hz, 1H), 7.72 (d, J = 16.0 Hz, 1H), 7.66 (d, J = 8.5 Hz, 2H), 7.46 (d, J = 8.5 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 6.95 (d, J = 9.0 Hz, 2H), 3.87 (s, 3H), 2.44 (s, 3H); 13 C NMR (125 MHz, CDCl 3 ) δ: 183.4, 162.4, 146.9, 143.5, 141.7, 136.4, 131.1, 130.2, 127.1, 122.7, 115.4, 114.5, 110.7, 55.5, 21.5; IR (KBr) ν: 2960, 2930, 2217, 1730, 1663, 1258, 1170, 1020 cm -1 + ; HRMS (ESI-TOF) calcd for C 19 H 17 N 2 O 2 ([M + H] + ): , found: (1E,3E)-2-oxo-4-phenyl-N-(p-tolyl)but-3-enimidoyl cyanide (3f): Yellow solid; m.p o C; 1 H NMR (CDCl 3, 500 MHz) δ: 7.97 (d, J = 16.0 Hz, 1H), 7.85 (d, J = 16.0 Hz, 1H), 7.69 (d, J = 7.5 Hz, 2H), 7.50 (d, J = 8.0 Hz, 2H), (m, 3H), 7.34 (d, J = 8.0 Hz, 2H), 2.45 (s, 3H); 13 C NMR (CDCl 3, 125 MHz) δ: 183.6, 146.9, 143.4, 142.0, 135.9, 134.3, 131.4, 130.2, 129.0, 129.0, 122.9, 117.9, 110.6, 21.5; IR (KBr) ν: 2962, 2938, 2218, 1738, 1670, 1261, 1176, 1032 cm -1 ; HRMS (ESI-TOF) calcd for C 18 H 15 N 2 O + ([M + H] + ): , found: (1E,3E)-4-(furan-2-yl)-2-oxo-N-(p-tolyl)but-3-enimidoyl cyanide (3g): S5

6 Yellow solid; m.p o C; 1 H NMR (500 MHz, CDCl 3 ) δ: 7.70 (s, 2H), 7.58 (s, 1H), 7.49 (d, J = 8.5 Hz, 2H), 7.34 (d, J = 8.5 Hz, 2H), 6.84 (d, J = 3.5 Hz, 1H), 6.56 (dd, J = 3.5, 1.6 Hz, 1H), 2.44 (s, 3H); 13 C NMR (125 MHz, CDCl 3 ) δ: 183.5, 151.4, 146.0, 143.4, 141.9, 135.8, 132.2, , 122.9, 118.3, 115.5, 113.1, 110.7, 21.5; HRMS (ESI-TOF) calcd for C 16 H 13 N 2 O 2 ([M + H] + ): , found: (1E,3E)-2-oxo-4-(thiophen-2-yl)-N-(p-tolyl)but-3-enimidoyl cyanide (3h): Yellow solid; m.p o C; 1 H NMR (CDCl 3, 500 MHz) δ: 2.44 (s, 3H), 7.12 (dd, J = 3.5, 5.0 Hz, 1H), 7.34 (d, J = 8.0 Hz, 2H), 7.45 (d, J = 2.0 Hz, 1H), 7.48 (d, J = 8.5 Hz, 2H), 7.50 (d, J = 5.0 Hz, 1H), 7.60 (d, J = 16.0 Hz, 1H), 8.07 (d, J = 15.5 Hz, 1H); 13 C NMR (CDCl 3, 125 MHz) δ: 183.2, 143.4, 141.9, 140.0, 139.1, 135.9, 133.5, 130.5, 130.2, 128.6, 122.9, 116.8, 110.7, 21.5; IR (KBr) ν: 2926, 2214, 1665, 1582, 1420, 1213, 1001 cm -1 ; HRMS (ESI-TOF) calcd for C 16 H 13 N 2 OS + ([M + H] + ): , found: (1E,3E)-4-(naphthalen-2-yl)-2-oxo-N-p-tolylbut-3-enimidoyl cyanide (3i): Yellow solid; m.p o C; 1 H NMR (500 MHz, CDCl 3 ) δ: 8.13 (d, J = 15.5 Hz, 1H), 8.09 (s, 1H), 7.95 (d, J = 16.0 Hz, 1H), (m, 4H), (m, 2H), 7.51 (d, J = 8.5 Hz, 2H), 7.35 (d, J = 8.0 Hz, 2H), 2.45 (s, 3H); 13 C NMR (125 MHz, CDCl 3 ) δ: 183.5, 147.0, 143.4, 141.9, 136.1, 134.7, 133.2, 131.9, 130.2, 128.8, 127.8, 127.7, 126.9, 123.7, 122.9, 118.0, 110.7, Two carbon is not visible due to overlapping peaks; IR (KBr) ν: 2920, 2217, 1666, 1598, 1567, 1363, 1302, 1200, 1002 cm -1 ; HRMS (ESI-TOF) calcd for C 22 H 17 N 2 O + ([M + H] + ): , found: S6

7 (1E,3E,5E)-2-oxo-6-phenyl-N-(p-tolyl)hexa-3,5-dienimidoyl cyanide (3j): O N CN Yellow solid; m.p o C; 1 H NMR (500 MHz, CDCl 3 ) δ: 7.74 (dd, J = 15.5, 11.0 Hz, 1H), 7.52 (d, J = 7.5 Hz, 2H), 7.47 (d, J = 8.5 Hz, 2H), (m, 4H), 7.33 (d, J = 8.0 Hz, 2H), 7.12 (d, J = 15.5 Hz, 1H), (m, 1H), 2.44 (s, 3H); 13 C NMR (125 MHz, CDCl 3 ) δ: 183.6, 146.9, 144.3, 143.4, 141.9, 135.9, 135.7, 130.2, 129.8, 128.9, 127.6, 126.7, 122.9, 121.3, 110.7, 21.5; HRMS (ESI-TOF) calcd for C 20 H 17 N 2 O + ([M + H] + ): , found: (1E,3E)-N,4-bis(4-chlorophenyl)-2-oxobut-3-enimidoyl cyanide (3k): Yellow solid; m.p o C; 1 H NMR (CDCl 3, 500 MHz) δ: 7.42 (d, J = 8.0 Hz, 2H), 7.46 (d, J = 8.5 Hz, 2H), 7.52 (d, J = 8.5 Hz, 2H), 7.63 (d, J = 8.0 Hz, 2H), 7.78 (d, J = 16.0 Hz, 1H), 7.92 (d, J = 16.0 Hz, 1H); 13 C NMR (CDCl 3, 125 MHz) δ: 183.0, 146.0, 144.2, 137.7, 137.6, 136.8, 132.6, 130.2, 129.9, 129.2, 123.7, 118.0, 110.0; IR (KBr) ν: 2923, 2208, 1668, 1607, 1487, 1335, 1092 cm -1 ; HRMS (ESI-TOF) calcd for C 17 H 11 Cl 2 N 2 O + ([M + H] + ): , found: (1E,3E)-4-(4-chlorophenyl)-2-oxo-N-phenylbut-3-enimidoyl cyanide (3l): O N CN Cl Yellow solid; m.p o C; 1 H NMR (500 MHz, CDCl 3 ) δ: 7.93 (d, J = 16.0 Hz, 1H), 7.82 (d, J = 16.0 Hz, 1H), 7.64 (d, J = 8.5 Hz, 2H), (m, 2H), (m, 3H), 7.42 (d, J = 8.5 Hz, 2H); 13 C NMR (125 MHz, CDCl 3 ) δ: 183.2, 146.0, 145.8, 137.6, 137.5, 132.6, 130.6, 130.2, S7

8 129.6, 129.4, 122.0, 118.1, 110.1; IR (KBr) ν: 2220, 1728, 1674, 1604, 1564, , 1208, 993 cm -1 ; HRMS (ESI-TOF) calcd for C 17 H 12 ClN 2 O + ([M + H] + ): , found: (1E,3E)-4-(4-chlorophenyl)-2-oxo-N-(m-tolyl)but-3-enimidoyl cyanide (3m): O N CN Cl Yellow solid; m.p o C; 1 H NMR (500 MHz, CDCl 3 ) δ: 7.92 (d, J = 16.0 Hz, 1H), 7.81 (d, J = 16.0 Hz, 1H), 7.63 (d, J = 8.5 Hz, 2H), (m, 3H), 7.29 (d, J = 5.5 Hz, 3H), 2.45 (s, 3H); 13 C NMR (125 MHz, CDCl 3 ) δ: 183.3, 146.0, 145.7, 139.7, 137.5, 137.2, 132.7, 131.5, 130.2, 129.4, 129.3, 122.8, 118.9, 118.2, 110.2, 21.3; IR (KBr) ν: 2922, 2217, 1667, 1598, 1563, 1329, 994 cm -1 ; HRMS (ESI-TOF) calcd for C 18 H 14 ClN 2 O + ([M + H] + ): , found: (1E,3E)-4-(4-chlorophenyl)-N-(4-methoxyphenyl)-2-oxobut-3-enimidoyl cyanide (3n): O N CN OMe Cl Yellow solid; m.p o C; 1 H NMR (500 MHz, CDCl 3 ) δ: 7.88 (d, J = 16.0 Hz, 1H), 7.84 (d, J = 16.0 Hz, 1H), 7.79 (d, J = 9.0 Hz, 2H), 7.62 (d, J = 8.5 Hz, 2H), 7.41 (d, J = 8.5 Hz, 2H), 7.05 (d, J = 9.0 Hz, 2H), 3.92 (s, 3H); 13 C NMR (125 MHz, CDCl 3 ) δ: 183.9, 162.9, 144.8, 138.2, 137.2, 132.9, 132.3, 130.1, 129.3, 126.8, 118.5, 114.9, 111.5, 55.8; IR (KBr) ν: 2917, 2208, 1667, 1608, 1535, 1312, 1271, 1167, 993 cm -1 + ; HRMS (ESI-TOF) calcd for C 18 H 14 ClN 2 O 2 ([M + H] + ): , found: S8

9 (E)-4-(4-chlorophenyl)-2-oxo-N-(p-tolyl)but-3-enamide (4a): Yellow solid; m.p o C; 1 H NMR (500 MHz, CDCl 3 ) δ: 8.93 (s, 1H), 7.94 (d, J = 16.0 Hz, 1H), 7.84 (d, J = 16.0 Hz, 1H), 7.62 (d, J = 8.5 Hz, 2H), 7.57 (d, J = 8.5 Hz, 2H), 7.41 (d, J = 8.5 Hz, 2H), 7.19 (d, J = 8.0 Hz, 2H), 2.34 (s, 3H); 13 C NMR (125 MHz, CDCl 3 ) δ: 185.4, 158.4, 146.9, 137.6, 134.9, 133.9, 132.7, 130.3, 129.6, 129.3, 119.7, 118.3, 20.9; HRMS (ESI-TOF) calcd + for C 17 H 15 ClNO 2 ([M + H] + ): , found: S9

10 III. General Procedure for the Preparation of 6 (6a as Example): R 1 O NH 2 N N R 2 NaOAc (1.2 eq) + CN AcOH, C NH 2 N 3 6 CN R 1 To a solution of (1E,3E)-4-(4-chlorophenyl)-2-oxo-N-(p-tolyl)but-3-enimidoyl cyanide 3a (0.20 mmol, 61.6 mg) in AcOH (2 ml) was added benzene-1,2-diamine (0.24 mmol, 25.9 mg) and NaOAc (0.24 mmol, 19.7 mg). Then the reaction mixture was stirred at 120 o C for 10 min. After 3a was consumed (monitored by TLC), the reaction mixture was poured into water (50 ml) and extracted with CH 2 Cl 2 (10 ml 3). The combined organic extracts were dried over anhydrous Na 2 SO 4, filtered and concentrated under reduced pressure to yield the corresponding crude product, which was purified by chromatography (silica gel, petroleum ether/acetone = 10/2, v/v) to give 6a (53.5 mg, 92%) as a yellow solid. (E)-3-(4-Chlorostyryl)quinoxaline-2-carbonitrile (6a): Yellow solid; m.p o C; 1 H NMR (500 MHz, CDCl 3 ) δ: 8.13 (d, J = 15.5 Hz, 1H), 8.08 (t, J = 8.5 Hz, 2H), 7.89 (t, J = 8.0 Hz, 1H), 7.79 (t, J = 8.0 Hz, 1H), 7.62 (d, J = 8.5 Hz, 2H), 7.60 (d, J = 15.5 Hz, 1H), 7.39 (d, J = 8.0 Hz, 2H); 13 C NMR (125 MHz, CDCl 3 ) δ: 150.2, 142.7, 140.9, 138.4, 135.8, 133.8, 133.5, 130.9, 129.6, 129.3, 129.2, 129.2, 129.1, 120.8, 115.6; IR (KBr) ν: 2221, 1615, 1535, 1456, 1355, 1228, 951, 860, 750, 718 cm -1 ; HRMS (ESI-TOF) calcd for + C 17 H 11 ClN 3 ([M + H] + ): , found: (E)-3-Styrylquinoxaline-2-carbonitrile (6f): S10

11 Yellow solid; m.p o C; 1 H NMR (500 MHz, CDCl 3 ) δ: 8.18 (d, J = 15.5 Hz, 1H), 8.08 (q, J = 8.5 Hz, 2H), 7.88 (t, J = 8.0 Hz, 1H), 7.77 (t, J = 7.5 Hz, 1H), 7.69 (d, J = 7.5 Hz, 2H), 7.64 (d, J = 16.0 Hz, 1H), (m, 3H); 13 C NMR (125 MHz, CDCl 3 ) δ: 150.5, 142.7, 140.8, 139.9, 135.3, 133.4, 130.7, 130.0, 129.5, 129.2, 129.1, 128.9, 128.0, 120.2, 115.6; HRMS (ESI-TOF) + calcd for C 17 H 12 N 3 ([M + H] + ): , found: (E)-3-(2-(Thiophen-2-yl)vinyl)quinoxaline-2-carbonitrile (6h): Yellow solid; m.p o C; 1 H NMR (500 MHz, CDCl 3 ) δ: 8.28 (d, J = 15.0 Hz, 1H), 8.04 (d, J = 9.0 Hz, 2H), 7.85 (t, J = 7.5 Hz, 1H), 7.75 (t, J = 7.5 Hz, 1H), 7.39 (d, J = 15.0 Hz, 1H), (m, 2H), 7.09 (t, J = 4.0 Hz, 1H); 13 C NMR (125 MHz, CDCl 3 ) δ: 150.4, 142.8, 140.9, 140.7, 133.4, 132.3, 130.6, 130.4, 129.5, 129.1, 128.8, 128.2, 128.1, 119.2, 115.5; IR (KBr) ν: 2219, 1606, , 1355, 1203, 958, 864, 756, 708 cm -1 ; HRMS (ESI-TOF) calcd for C 15 H 10 N 3 S + ([M + H] + ): , found: S11

12 IV. Crystal ORTEP drawing of compound 3a: S12

13 V. Copies of 1 H NMR and 13 C NMR spectra of compounds 3, 4 and 6: Figure 1. 1 H- (upper) and 13 C-NMR (lower) spectra of compound 3a. S13

14 Figure 2. 1 H- (upper) and 13 C-NMR (lower) spectra of compound 3b. S14

15 Figure 3. 1 H- (upper) and 13 C-NMR (lower) spectra of compound 3c. S15

16 Figure 4. 1 H- (upper) and 13 C-NMR (lower) spectra of compound 3d. S16

17 Figure 5. 1 H- (upper) and 13 C-NMR (lower) spectra of compound 3e. S17

18 Figure 6. 1 H- (upper) and 13 C-NMR (lower) spectra of compound 3f. S18

19 Figure 7. 1 H- (upper) and 13 C-NMR (lower) spectra of compound 3g. S19

20 Figure 8. 1 H- (upper) and 13 C-NMR (lower) spectra of compound 3h. S20

21 Figure 9. 1 H- (upper) and 13 C-NMR (lower) spectra of compound 3i. S21

22 Figure H- (upper) and 13 C-NMR (lower) spectra of compound 3j. S22

23 Figure H- (upper) and 13 C-NMR (lower) spectra of compound 3k. S23

24 Figure H- (upper) and 13 C-NMR (lower) spectra of compound 3l. S24

25 Figure H- (upper) and 13 C-NMR (lower) spectra of compound 3m. S25

26 Figure H- (upper) and 13 C-NMR (lower) spectra of compound 3n. S26

27 Figure H- (upper) and 13 C-NMR (lower) spectra of compound 4a. S27

28 Figure H- (upper) and 13 C-NMR (lower) spectra of compound 6a. S28

29 Figure H- (upper) and 13 C-NMR (lower) spectra of compound 6f. S29

30 Figure H- (upper) and 13 C-NMR (lower) spectra of compound 6h. S30

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Information Regiodivergent Heterocyclization: A Strategy for the Synthesis of Substituted Pyrroles and Furans Using α-formyl Ketene Dithioacetals as Common Precursors Ting Wu,

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

Hai-Bin Yang, Xing Fan, Yin Wei,* Min Shi*

Hai-Bin Yang, Xing Fan, Yin Wei,* Min Shi* Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2015 Solvent-controlled Nucleophilic Trifloromethylthiolation of Morita- Baylis-Hillman

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

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

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Rh 2 (Ac) 4 -Catalyzed 2,3-Migration of -rrocenecarboxyl -Diazocarbonyl

More information

*Corresponding author. Tel.: , ; fax: ; Materials and Method 2. Preparation of GO nanosheets 3

*Corresponding author. Tel.: , ; fax: ; Materials and Method 2. Preparation of GO nanosheets 3 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Synthesis of 2,3-dihydroquinazolinones and quinazolin-4(3h)-one catalyzed by Graphene Oxide

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

N-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides

N-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Electronic supplementary information for -Hydroxyphthalimide: a new photoredox catalyst for [4+1]

More information

Silver-Catalyzed Cascade Reaction of β-enaminones and Isocyanoacetates to Construct Functionalized Pyrroles

Silver-Catalyzed Cascade Reaction of β-enaminones and Isocyanoacetates to Construct Functionalized Pyrroles Supporting Information for Silver-Catalyzed Cascade Reaction of β-enaminones and Isocyanoacetates to Construct Functionalized Pyrroles Guichun Fang, a, Jianquan Liu a,c, Junkai Fu,* a Qun Liu, a and Xihe

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

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 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

Nanocrystalline Magnesium Oxide-Stabilized Palladium(0): An Efficient and Reusable Catalyst for the Synthesis of N-(2- pyridyl)indoles

Nanocrystalline Magnesium Oxide-Stabilized Palladium(0): An Efficient and Reusable Catalyst for the Synthesis of N-(2- pyridyl)indoles Electronic Supplementary Material (ESI) for ew Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre ational de la Recherche Scientifique 2015 Supplementary Material (ESI)

More information

Total Synthesis of Gonytolides C and G, Lachnone C, and. Formal Synthesis of Blennolide C and Diversonol

Total Synthesis of Gonytolides C and G, Lachnone C, and. Formal Synthesis of Blennolide C and Diversonol . This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry Total Synthesis of Gonytolides C and G, Lachnone C, and Formal Synthesis

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

A Sumanene-based Aryne, Sumanyne

A Sumanene-based Aryne, Sumanyne A Sumanene-based Aryne, Sumanyne Niti Ngamsomprasert, Yumi Yakiyama, and Hidehiro Sakurai* Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871

More information

Singapore, #05 01, 28 Medical Drive, Singapore. PR China,

Singapore, #05 01, 28 Medical Drive, Singapore. PR China, Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2017 Catalyst controlled Regioselectivity in Phosphine Catalysis: Synthesis of Spirocyclic Benzofuranones

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

Supplementary Information

Supplementary Information Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)

More information

Halogen halogen interactions in diiodo-xylenes

Halogen halogen interactions in diiodo-xylenes Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) for CrystEngComm. This journal is The Royal Society

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Supporting Information Merging visible-light photoredox and copper catalysis

More information

Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous media

Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous media Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous

More information

Supporting Information

Supporting Information Supporting Information Electrooxidative C(sp3) H Amination of Azoles via Intermolecular Oxidative C(sp3) H/N H Cross-Coupling Jiwei Wu, Yi Zhou, Yuchen Zhou, Chien-Wei Chiang Aiwen Lei* The Institute for

More information

Synthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity

Synthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity Supporting Information for Synthesis of Glaucogenin D, a Structurally Unique Disecopregnane Steroid with Potential Antiviral Activity Jinghan Gui,* Hailong Tian, and Weisheng Tian* Key Laboratory of Synthetic

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

Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene

Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene Seyoung Choi and Sangho Koo* Department of Chemistry, Myong Ji University, Yongin, Kyunggi-Do, 449-728, Korea. E-mail:

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

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany A Highly Enantioselective Brønsted Acid Catalyst for the Strecker Reaction Magnus Rueping, * Erli Sugiono and Cengiz Azap General: Unless otherwise

More information

PTSA-Catalyzed Green Synthesis of 1,3,5-Triarylbenzene under Solvent-Free Conditions

PTSA-Catalyzed Green Synthesis of 1,3,5-Triarylbenzene under Solvent-Free Conditions S1 Supporting Information PTSA-Catalyzed Green Synthesis of 1,3,5-Triarylbenzene under Solvent-Free Conditions Yanan Zhao, a Jian Li, a Chunju Li, a Kun Yin, a Dongyan Ye a and Xueshun Jia*, a, b a Department

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 ne-pot synthesis of pyrrolidino- and piperidinoquinolinones by three-component aza-diels Alder reactions of -arylimines with in situ generated cyclic enamides. Wenxue Zhang, Yisi Dai, Xuerui Wang, Wei

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2017 Supporting Information Direct copper-catalyzed oxidative trifluoromethylthiolation

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

Supporting Information. Cu(I)-Catalyzed Three-Component Reaction of Diazo. Compound with Terminal Alkyne and Nitrosobenzene for

Supporting Information. Cu(I)-Catalyzed Three-Component Reaction of Diazo. Compound with Terminal Alkyne and Nitrosobenzene for Supporting Information of Cu(I)-Catalyzed Three-Component Reaction of Diazo Compound with Terminal Alkyne and Nitrosobenzene for the Synthesis of Trifluoromethyl Dihydroisoxazoles Xinxin Lv, Zhenghui Kang,

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

pyrazoles/isoxazoles library using ketene dithioacetals

pyrazoles/isoxazoles library using ketene dithioacetals Water mediated construction of trisubstituted pyrazoles/isoxazoles library using ketene dithioacetals Mahesh M. Savant, Akshay M. Pansuriya, Chirag V. Bhuva, Naval Kapuriya, Anil S. Patel, Vipul B. Audichya,

More information

Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine

Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine Ying Xie, a Hongjie Pan, a Xiao Xiao, a Songlei Li a and Yian Shi* a,b a Beijing National Laboratory for

More information

Supporting Information. Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using Acetonitrile as Cyanide Source

Supporting Information. Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using Acetonitrile as Cyanide Source Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2015 Supporting Information Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using

More information

Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol

Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol S1 Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2010 Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol Julien

More information

Aggregation-induced emission enhancement based on 11,11,12,12,-tetracyano-9,10-anthraquinodimethane

Aggregation-induced emission enhancement based on 11,11,12,12,-tetracyano-9,10-anthraquinodimethane Electronic Supplementary Information (ESI) Aggregation-induced emission enhancement based on 11,11,12,12,-tetracyano-9,10-anthraquinodimethane Jie Liu, ab Qing Meng, a Xiaotao Zhang, a Xiuqiang Lu, a Ping

More information

Prabhat Gautam, Bhausaheb Dhokale, Shaikh M. Mobin and Rajneesh Misra*

Prabhat Gautam, Bhausaheb Dhokale, Shaikh M. Mobin and Rajneesh Misra* Supporting Information Ferrocenyl BODIPYs: Synthesis, Structure and Properties Prabhat Gautam, Bhausaheb Dhokale, Shaikh M. Mobin and Rajneesh Misra* Department of Chemistry, Indian Institute of Technology

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

Organocatalytic Doubly Annulative Approach to 3,4-Dihydrocoumarins Bearing a Fused Pyrrolidine Scaffold. Dorota Kowalczyk, and Łukasz Albrecht*

Organocatalytic Doubly Annulative Approach to 3,4-Dihydrocoumarins Bearing a Fused Pyrrolidine Scaffold. Dorota Kowalczyk, and Łukasz Albrecht* Organocatalytic Doubly Annulative Approach to 3,4-Dihydrocoumarins Bearing a Fused Pyrrolidine Scaffold Dorota Kowalczyk, and Łukasz Albrecht* Institute of Organic Chemistry, Chemistry Department, Lodz

More information

Supporting Information. Cells. Mian Wang, Yanglei Yuan, Hongmei Wang* and Zhaohai Qin*

Supporting Information. Cells. Mian Wang, Yanglei Yuan, Hongmei Wang* and Zhaohai Qin* Electronic Supplementary Material (ESI) for Analyst. This journal is The Royal Society of Chemistry 2015 Supporting Information Fluorescent and Colorimetric Probe Containing Oxime-Ether for Pd 2+ in Pure

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2015 A rare case of a dye co-crystal showing better dyeing performance Hui-Fen Qian, Yin-Ge Wang,

More information

Supporting Information for. an Equatorial Diadduct: Evidence for an Electrophilic Carbanion

Supporting Information for. an Equatorial Diadduct: Evidence for an Electrophilic Carbanion Supporting Information for Controlled Synthesis of C 70 Equatorial Multiadducts with Mixed Addends from an Equatorial Diadduct: Evidence for an Electrophilic Carbanion Shu-Hui Li, Zong-Jun Li,* Wei-Wei

More information

Cu-Catalyzed Synthesis of 3-Formyl imidazo[1,2-a]pyridines. and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary

Cu-Catalyzed Synthesis of 3-Formyl imidazo[1,2-a]pyridines. and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary Cu-Catalyzed Synthesis of 3-Formyl imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary Amines as Carbon Sources Changqing Rao, Shaoyu Mai and Qiuling Song* Institute of Next

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

The all-photochemical Synthesis an. OGP (10-14) Precursor

The all-photochemical Synthesis an. OGP (10-14) Precursor SUPPORTING INFORMATION The all-photochemical Synthesis an OGP (10-14) Precursor Jean-Luc Débieux, Christian G. Bochet* Department of Chemistry, University of Fribourg, 9 Chemin du Musée, CH-1700 Fribourg,

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

Supporting Information. Expeditious Construction of the DEF Ring System of Thiersinine B

Supporting Information. Expeditious Construction of the DEF Ring System of Thiersinine B Supporting Information Expeditious Construction of the DEF Ring System of Thiersinine B Masaru Enomoto and Shigefumi Kuwahara* Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural

More information

Fluorescent Chemosensor for Selective Detection of Ag + in an. Aqueous Medium

Fluorescent Chemosensor for Selective Detection of Ag + in an. Aqueous Medium Electronic supplementary information For A Heptamethine cyanine -Based Colorimetric and Ratiometric Fluorescent Chemosensor for Selective Detection of Ag + in an Aqueous Medium Hong Zheng *, Min Yan, Xiao-Xing

More information

Halogen bonded dimers and ribbons from the self-assembly of 3-halobenzophenones Patricia A. A. M. Vaz, João Rocha, Artur M. S. Silva and Samuel Guieu

Halogen bonded dimers and ribbons from the self-assembly of 3-halobenzophenones Patricia A. A. M. Vaz, João Rocha, Artur M. S. Silva and Samuel Guieu Electronic Supplementary Material (ES) for CrystEngComm. This journal is The Royal Society of Chemistry 27 Halogen bonded dimers and ribbons from the self-assembly of -halobenzophenones Patricia A. A.

More information

SYNTHESIS AND ANTIBACTERIAL EVALUATION OF NOVEL 3,6- DISUBSTITUTED COUMARIN DERIVATIVES

SYNTHESIS AND ANTIBACTERIAL EVALUATION OF NOVEL 3,6- DISUBSTITUTED COUMARIN DERIVATIVES SYNTHESIS AND ANTIBACTERIAL EVALUATION OF NOVEL 3,6- DISUBSTITUTED COUMARIN DERIVATIVES 1 Ravibabu Velpula, 1 Ramesh Gondru, 2 Yashodhara Velivela and 1 Rajitha Bavantula* 1 Department of Chemistry, National

More information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Visible light-mediated dehydrogenative

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2019 Supporting Information Difluorocarbene-derived trifluoromethylselenolation of benzyl halides Xin-Lei

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

A selenium-contained aggregation-induced turn-on fluorescent probe for hydrogen peroxide

A selenium-contained aggregation-induced turn-on fluorescent probe for hydrogen peroxide Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information (ESI) A selenium-contained aggregation-induced

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 208 Supporting Information Cobalt-Catalyzed Regioselective Syntheses of Indeno[2,-c]pyridines

More information

Supporting information

Supporting information Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 205 A simple and greener approach

More information

Supporting Information

Supporting Information Efficient Greenish Blue Electrochemiluminescence from Fluorene and Spirobifluorene Derivatives Federico Polo, *,, Fabio Rizzo, *, Manoel Veiga Gutierrez, Luisa De Cola, Silvio Quici Physikalisches Institut,

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

Supporting Information

Supporting Information Supporting Information Catalyst- and solvent-free one-pot synthesis of some novel polyheterocycles from aryldiazenyl salicylaldehyde derivatives Narsidas J. Parmar 1, Rikin A. Patel 1, Shashikant B. Teraiya

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

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

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

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

Recyclable Enamine Catalysts for Asymmetric Direct Cross-Aldol

Recyclable Enamine Catalysts for Asymmetric Direct Cross-Aldol Recyclable Enamine Catalysts for Asymmetric Direct Cross-Aldol Reaction of Aldehydes in Emulsion Media Qiang Gao, a,b Yan Liu, a Sheng-Mei Lu, a Jun Li a and Can Li* a a State Key Laboratory of Catalysis,

More information

A Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones. Jin-Quan Yu, a and E. J.

A Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones. Jin-Quan Yu, a and E. J. A Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones Jin-Quan Yu, a and E. J. Corey b * a Department of Chemistry, Cambridge University, Cambridge CB2 1EW, United

More information

Supporting Information

Supporting Information Supporting Information Enantioselective Synthesis of 3-Alkynyl-3-Hydroxyindolin-2-ones by Copper-Catalyzed Asymmetric Addition of Terminal Alkynes to Isatins Ning Xu, Da-Wei Gu, Jing Zi, Xin-Yan Wu, and

More information

Supporting Information:

Supporting Information: Supporting Information: An rganocatalytic Asymmetric Sequential Allylic Alkylation/Cyclization of Morita-Baylis-Hillman Carbonates and 3-Hydroxyoxindoles Qi-Lin Wang a,b, Lin Peng a, Fei-Ying Wang a, Ming-Liang

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

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

Asymmetric Organocatalytic Strecker-Type Reactions of Aliphatic N,N- Dialkylhydrazones

Asymmetric Organocatalytic Strecker-Type Reactions of Aliphatic N,N- Dialkylhydrazones Asymmetric Organocatalytic Strecker-Type Reactions of Aliphatic N,N- Dialkylhydrazones Aurora Martínez-Muñoz, David Monge,* Eloísa Martín-Zamora, Eugenia Marqués-López, Eleuterio Álvarez, Rosario Fernández,*

More information

Supporting Information

Supporting Information 1 Supporting Information Gold-catalyzed Synthesis of 3-arylindoles via Annulation of Nitrosoarenes and Alkynes Siva Murru, August A. Gallo and Radhey S. Srivastava* Department of Chemistry, University

More information

Electronic Supplementary Information (12 pages)

Electronic Supplementary Information (12 pages) Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A C 2 -responsive pillar[5]arene: synthesis and self-assembly in water Kecheng Jie, Yong Yao, Xiaodong

More information

Yujuan Zhou, Kecheng Jie and Feihe Huang*

Yujuan Zhou, Kecheng Jie and Feihe Huang* Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 A redox-responsive selenium-containing pillar[5]arene-based macrocyclic amphiphile: synthesis,

More information

Synthesis of Aminophenanthrenes and Benzoquinolines via Hauser-Kraus Annulation of Sulfonyl Phthalide with Rauhut- Currier Adducts of Nitroalkenes

Synthesis of Aminophenanthrenes and Benzoquinolines via Hauser-Kraus Annulation of Sulfonyl Phthalide with Rauhut- Currier Adducts of Nitroalkenes Synthesis of Aminophenanthrenes and Benzoquinolines via Hauser-Kraus Annulation of Sulfonyl Phthalide with Rauhut- Currier Adducts of Nitroalkenes Tarun Kumar, Vaijinath Mane and Irishi N. N. Namboothiri*

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2017 Supporting Information Lithium Triethylborohydride-Promoted Generation of α,α-difluoroenolates

More information

Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure

Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via Chiral Transfer of the Conjugated

More information

Electronic Supplementary Information for Catalytic Asymmetric Hydrophosphonylation of Ynones

Electronic Supplementary Information for Catalytic Asymmetric Hydrophosphonylation of Ynones Electronic Supplementary Information for Catalytic Asymmetric Hydrophosphonylation of Ynones Daisuke Uraguchi, Takaki Ito, Shinji Nakamura, and Takashi oi* Department of Applied Chemistry, Graduate School

More information

Supporting Information

Supporting Information Supporting Information for Cu-Mediated trifluoromethylation of benzyl, allyl and propargyl methanesulfonates with TMSCF 3 Xueliang Jiang 1 and Feng-Ling Qing* 1,2 Address: 1 Key Laboratory of Organofluorine

More information

Experimental and Theoretical Investigations of. Surface-Assisted Graphene Nanoribbon Synthesis

Experimental and Theoretical Investigations of. Surface-Assisted Graphene Nanoribbon Synthesis Experimental and Theoretical Investigations of Surface-Assisted Graphene Nanoribbon Synthesis Featuring Carbon Fluorine Bond Cleavage Hironobu Hayashi,,, * Junichi Yamaguchi,, Hideyuki Jippo, Ryunosuke

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

Rare double spin canting antiferromagnetic behaviours in a. [Co 24 ] cluster

Rare double spin canting antiferromagnetic behaviours in a. [Co 24 ] cluster Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Rare double spin canting antiferromagnetic behaviours in a [Co 24 ] cluster Guang-Ming Liang, Qing-Ling

More information

Supporting Information. An AIE active Y-shaped diimidazolylbenzene: aggregation and

Supporting Information. An AIE active Y-shaped diimidazolylbenzene: aggregation and Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information An AIE active Y-shaped diimidazolylbenzene: aggregation

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

Tsuji Trost N-Allylation with Allylic Acetates by Using a Cellulose Palladium Catalyst

Tsuji Trost N-Allylation with Allylic Acetates by Using a Cellulose Palladium Catalyst University of Nebraska - Lincoln DigitalCommons@University of Nebraska - Lincoln U.S. Environmental Protection Agency Papers U.S. Environmental Protection Agency 2012 Tsuji Trost N-Allylation with Allylic

More information

Supplementary Figure S1 X-ray crystallographic structure of (C)-(-)-6. (a) ORTEP drawing of (C)-(-)-6 at probability ellipsoids of 50%: tope view.

Supplementary Figure S1 X-ray crystallographic structure of (C)-(-)-6. (a) ORTEP drawing of (C)-(-)-6 at probability ellipsoids of 50%: tope view. Supplementary Figure S1 X-ray crystallographic structure of (C)-(-)-6. (a) ORTEP drawing of (C)-(-)-6 at probability ellipsoids of 50%: tope view. (b) Side view. All hydrogen atoms are omitted for clarity.

More information

Amide Directed Cross-Coupling between Alkenes and Alkynes: A Regio- and Stereoselective Approach to Substituted (2Z,4Z)-Dienamides

Amide Directed Cross-Coupling between Alkenes and Alkynes: A Regio- and Stereoselective Approach to Substituted (2Z,4Z)-Dienamides Supporting Information For the article entitled Amide Directed Cross-Coupling between Alkenes and Alkynes: A Regio- and Stereoselective Approach to Substituted (2Z,4Z)-Dienamides Keke Meng, Jian Zhang,*

More information

Synthesis of two novel indolo[3,2-b]carbazole derivatives with aggregation-enhanced emission property

Synthesis of two novel indolo[3,2-b]carbazole derivatives with aggregation-enhanced emission property Supporting Information for: Synthesis of two novel indolo[3,2-b]carbazole derivatives with aggregation-enhanced emission property Wen-Bin Jia, Hao-Wei Wang, Long-Mei Yang, Hong-Bo Lu, Lin Kong, Yu-Peng

More information

Electronic Supplementary Material

Electronic Supplementary Material Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material A Novel Functionalized Pillar[5]arene: Synthesis, Assembly

More information

Organocatalytic asymmetric synthesis of 3,3-disubstituted oxindoles featuring two heteroatoms at C3 position

Organocatalytic asymmetric synthesis of 3,3-disubstituted oxindoles featuring two heteroatoms at C3 position Organocatalytic asymmetric synthesis of 3,3-disubstituted oxindoles featuring two heteroatoms at C3 position Feng Zhou, Xing-Ping Zeng, Chao Wang, Xiao-Li Zhao, and Jian Zhou* [a] Shanghai Key Laboratory

More information

Supporting Information

Supporting Information Supporting Information Brønsted Acid-Catalyzed [6+2]-Cycloaddition of 2-Vinylindoles with In Situ Generated 2-Methide-2H-pyrroles: Direct, Catalytic, and Enantioselective Synthesis of 2,3-Dihydro-H-pyrrolizines

More information

Well-organized Supramolecular Self-Assembly of a Novel Acene Diimide Derivatives

Well-organized Supramolecular Self-Assembly of a Novel Acene Diimide Derivatives Well-organized Supramolecular Self-Assembly of a Novel Acene Diimide Derivatives Sheshanath V. Bhosale, a, * Mohammad Al Kobaisi, a Rajesh S. Bhosale b and Sidhanath V. Bhosale b a Supramolecular Chemistry

More information

Supporting Information

Supporting Information Supporting Information Manuscript Title: Synthesis of Semibullvalene Derivatives via Co 2 (CO) 8 -Mediated Cyclodimerization of 1,4-Dilithio-1,3-butadienes Corresponding Author: Zhenfeng Xi Affiliations:

More information

Highly stereocontrolled synthesis of trans-enediynes via

Highly stereocontrolled synthesis of trans-enediynes via Supporting Information for Highly stereocontrolled synthesis of trans-enediynes via carbocupration of fluoroalkylated diynes Tsutomu Konno*, Misato Kishi, and Takashi Ishihara Address: Department of Chemistry

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

Supplementary Figure 1. 1 H and 13 C NMR spectra for compound 1a

Supplementary Figure 1. 1 H and 13 C NMR spectra for compound 1a 216.29 185.02 164.20 148.97 128.19 87.70 79.67 77.30 77.04 76.79 74.66 26.23 2.02 2.03 2.01 3.05 7.26 6.92 6.90 6.25 6.23 5.61 5.60 5.58 5.25 5.24 1.58 Supplementary Figure 1. 1 H and 13 C NMR spectra

More information