Supporting Information
|
|
|
- Jasmine Lindsey
- 5 years ago
- Views:
Transcription
1 S1 Dehydrogenative Coupling Reactions Catalysed by Rose Bengal Using Visible Light Irradiation Yuanhang Pan, Choon Wee Kee, Li Chen and Choon-Hong Tan* Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, chmtanch@nus.edu.sg Supporting Information General procedures and methods Experimental procedure for dehydrogenative nitro-mannich reaction Experimental procedure for dehydrogenative Mannich reaction Fluorescence quenching study of RB by tertiary amine Copies of NMR spectra Computational Details S2 S3 S5 S7 S8 S9 References S40
2 S2 General procedures and methods 1 H and 13 C NMR spectra were recorded on a Bruker ACF300 (300MHz), Bruker DPX300 (300MHz) DRX500 (500MHz) or AMX500 (500MHz) spectrometer. Chemical shifts are reported in parts per million (ppm). The residual solvent peak was used as an internal reference. Low resolution mass spectra were obtained on a Finnigan/MAT LCQ spectrometer in ESI mode and a Finnigan/MAT 95XL-T mass spectrometer in FAB mode. All high resolution mass spectra were obtained on a Finnigan/MAT 95XL-T spectrometer. Analytical thin layer chromatography (TLC) was performed with Merck pre-coated TLC plates, silica gel 60F-254, layer thickness 0.25 mm. Flash chromatography separations were performed on Merck 60 ( mm) mesh silica gel. Reagents and solvents were commercial grade and were used as supplied without further purification, unless otherwise stated. Irradiation with green light was performed using 0.5-5W LEDs. LEDs were bought from LED POWER SUPPLY, CE-IKEA, TYPE: SLT5-12V. Fluorosence spectra was recorded using SHIMADZU RF-5301.
3 S3 Representative procedure for oxidative dehydrogenative nitro-mannich reaction between N-aryl-tetrahydroisoquinoline 1a and nitromethane catalyzed by Rose Bengal 1a (20.9 mg, 0.1 mmol, 1.0 equiv.) was added to a solution of RB (5.0 mg, mmol, 5 mol%) in 1.0 ml nitromethane 2a. The reaction mixture was stirred under green LEDs irradiation at room temperature. After 10 hours, the solvent was removed in vacuo and the crude product was directly loaded onto a short silica gel column. Flash chromatography was performed using gradient elution with hexane/ea mixtures (40/1-15/1 ratio). After removing solvent, product 3a (24.7 mg) was obtained as yellow oil in 92% yield. 1-(nitromethyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline (3a) [1] yellow oil, 1 H NMR (500 MHz, CDCl 3, ppm) δ (m, 5H), 7.15 (d, J = 7.4 Hz, 1H), 7.00 (d, J = 8.0 Hz, 2H), 6.86 (t, J = 7.2 Hz, 1H), 5.56 (t, J = 7.2 Hz, 1H), 4.88 (dd, J = 11.8, 7.8 Hz, 1H), 4.57 (dd, J = 11.9, 6.7 Hz, 1H), (m, 2H), (m, 1H), (m, 1H). LRMS (ESI) m/z (M + H + ). 1-(1-nitroethyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline (3b) [1] yellow oil, dr = 3:2, 1 H NMR (500 MHz, CDCl 3, ppm) mixture of the two diastereoisomers: δ (m, 6H), (m, 2H), (m, 1H), (m, 1H), (m, 0.6H, major isomer), (m, 0.4H, minor isomer), (m, 0.7H), (m, 1.4H), (m, 1H), (m, 1H), 1.70 (d, J = 6.9 Hz, 1.2H, minor isomer), 1.54 (d, J = 7.6 Hz, 1.8H, major isomer). LRMS (ESI) m/z (M + H + ). 1-(1-nitropropyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline (3c) [2] yellow oil, dr = 3:2, 1 H NMR (500 MHz, CDCl 3, ppm) mixture of the two diastereoisomers: δ (m, 6H), (m, 2H), (m, 1H), 5.25 (d, J = 9.2 Hz, 0.3H, minor isomer), 5.14 (d, J = 9.5 Hz, 0.5H, major isomer), (m, 0.4H, major isomer), (m, 0.3H, minor isomer), (m, 0.4H), (m, 2H), (m, 2H), (m, 1.5H), (m, 0.5H), (m, 3H). LRMS (ESI) m/z (M + H + ). 2-(4-bromophenyl)-1-(nitromethyl)-1,2,3,4-tetrahydroisoquinoline (3d) [3] yellow oil, 1 H NMR (500 MHz, CDCl 3, ppm) δ (m, 2H), (m, 3H), 7.14 (d, J = 7.3 Hz, 1H), 6.85 (d, J = 9.1 Hz, 2H),
4 S (t, J = 7.2 Hz, 1H), 4.84 (dd, J = 12.0, 8.1 Hz, 1H), 4.57 (dd, J = 12.0, 6.4 Hz, 1H), (m, 2H), (m, 1H), 2.79 (dt, J = 16.4, 4.8 Hz, 1H). LRMS (ESI) m/z , (M + H + ). 1-(nitromethyl)-2-(p-tolyl)-1,2,3,4-tetrahydroisoquinoline (3e) [3] yellow oil, 1 H NMR (500 MHz, CDCl 3, ppm) δ (m, 4H), 7.08 (d, J = 8.4 Hz, 2H), 6.90 (d, J = 8.6 Hz, 2H), 5.50 (t, J = 7.2 Hz, 1H), 4.85 (dd, J = 11.9, 8.1 Hz, 1H), 4.56 (dd, J = 11.9, 6.4 Hz, 1H), (m, 2H), (m, 1H), 2.76 (dt, J = 16.4, 4.5 Hz, 1H), 2.27 (s, 3H). LRMS (ESI) m/z (M + H + ). N,4-dimethyl-N-(2-nitroethyl)aniline (3f) [1] yellow oil, 1 H NMR (500 MHz, CDCl 3, ppm) δ 7.08 (d, J = 8.4 Hz, 2H), 6.67 (d, J = 8.6 Hz, 2H), 4.56 (t, J = 6.4 Hz, 2H), 3.96 (t, J = 6.4 Hz, 2H), 2.95 (s, 3H), 2.27 (s, 3H). LRMS (ESI) m/z (M + H + ).
5 S5 Representative procedure for dehydrogenative Mannich reaction between N-aryl-tetrahydroisoquinoline 1a and acetone catalyzed by Rose Bengal 1a (20.9 mg, 0.1 mmol, 1.0 equiv.) was added to a solution of RB (5.0 mg, mmol, 5 mol%) in 1.0 ml acetone 4a, followed by adding pyrrolidine (2.5 ul, 0.03 mmol, 30 mol%) and TFA (2.3 ul, 0.03 mmol, 30 mol%). The reaction mixture was stirred under green LEDs irradiation at room temperature. After 20 hours. the solvent was removed in vacuo and the crude product was directly loaded onto a short silica gel column. Flash chromatography was performed using gradient elution with hexane/ea mixtures (40/1-15/1 ratio). After removing solvent, product 5a (24.1 mg) was obtained as pale yellow solid in 91% yield. 1-(2-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl)propan-2-one (5a) [4] pale yellow solid, 1 H NMR (500 MHz, CDCl 3, ppm) δ (m, 6H), 6.95 (d, J = 8.2 Hz, 2H), 6.79 (t, J = 7.3 Hz, 1H), 5.41 (t, J = 6.3 Hz, 1H), (m, 1H), (m, 1H), (m, 2H), (m, 2H), 2.08 (s, 3H). LRMS (ESI) m/z (M + H + ). 1-(2-(4-bromophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)propan-2-one (5b) [5] yellow oil, 1 H NMR (500 MHz, CDCl 3, ppm) δ (m, 2H), (m, 4H), (m, 2H), 5.35 (t, J = 6.3 Hz, 1H), (m, 1H), (m, 1H), (m, 2H), (m, 2H), 2.08 (s, 3H). 13 C NMR (125 MHz, CDCl 3, ppm) δ 206.9, 147.8, 137.9, 134.2, 132.0, 128.6, 127.0, 126.8, 126.4, 116.1, 110.1, 77.2, 77.0, 76.7, 54.6, 50.1, 42.1, 31.1, LRMS (ESI) m/z (M + H + ), HRMS (ESI) m/z calc. for C 18 H BrNO, calc. for C 18 H BrNO. 1-(2-p-tolyl-1,2,3,4-tetrahydroisoquinolin-1-yl)propan-2-one (5c) [5] yellow oil, 1 H NMR (500 MHz, CDCl 3, ppm) δ (m, 4H), 7.05 (d, J = 8.5 Hz, 2H), 6.86 (d, J = 8.5 Hz, 2H), 5.34 (t, J = 6.4 Hz, 1H), (m, 1H), (m, 1H), (m, 2H), (m, 2H), 2.25 (s, 3H), 2.07 (s, 3H). LRMS (ESI) m/z (M + H + ). 1-(2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)propan-2-one (5d) [4]
6 S6 (M + H + ). yellow oil, 1 H NMR (500 MHz, CDCl 3, ppm) δ (m, 4H), (m, 2H), (m, 2H), 5.25 (t, J = 6.4 Hz, 1H), 3.75 (s, 3H), (m, 1H), (m, 1H), (m, 2H), (m, 2H), 2.06 (s, 3H). LRMS (ESI) m/z (2-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl)butan-2-one (5e) [4] yellow oil, 1 H NMR (500 MHz, CDCl 3, ppm) δ (m, 2H), (m, 4H), 6.95 (d, J = 8.2 Hz, 2H), 6.77 (t, J = 7.2 Hz, 1H), 5.42 (t, J = 6.4 Hz, 1H), (m, 1H), (m, 1H), (m, 2H), (m, 2H), (m, 2H), 0.99 (t, J = 7.3 Hz, 3H). LRMS (ESI) m/z (M + H + ). Procedure for L-Proline and Rose Bengal co-catalyzed oxidative Mannich reaction between N-aryl-tetrahydroisoquinoline 1d and cyclohexanone 4c 1d (23.9 mg, 0.1 mmol, 1.0 equiv.) was added to a solution of RB (5.0 mg, mmol, 5 mol%) in 1.0 ml CH 3 CN, followed by adding cyclohexanone 4c (103.5 ul, 1.0 mmol, 10.0 equiv.) and L-Proline (3.5 mg, 0.03 mmol, 30 mol%). The reaction mixture was stirred under green LEDs irradiation at room temperature. After 60 hours. the solvent was removed in vacuo and the crude product was directly loaded onto a short silica gel column. Flash chromatography was performed using gradient elution with hexane/ea mixtures (40/1-15/1 ratio). After removing solvent, product 5f (22.1 mg) was obtained as yellow solid in 66% yield with 9:1 dr. yellow solid, 1 H NMR (500 MHz, CDCl 3, ppm) major isomer (syn): δ (m, 4H), 6.88 (d, J = 9.0 Hz, 2H), 6.79 (d, J = 9.1 Hz, 2H), 5.36 (d, J = 5.5 Hz, 1H), 3.74 (s, 3H), (m, 1H), (m, 1H), (m, 3H), (m, 1H), (m, 1H), (m, 6H). 13 C NMR (75 MHz, CDCl 3, ppm) major isomer (syn): δ 212.3, 153.3, 144.2, 136.4, 135.3, 129.1, 128.0, 126.8, 125.8, 118.5, 114.8, 77.6, 77.2, 76.8, 56.6, 56.1, 55.8, 44.1, 41.3, 30.5, 27.7, 26.8, LRMS (ESI) m/z (M + H + ), HRMS (ESI) m/z calc. for C 22 H 26 NO
7 S7 Fluorescence quenching study of RB by tertiary amine Black curve shows the fluorescence spectra of RB (1.6 um in CH 3 CN). Excited at 510nm, PL: 589 nm. Pink curve shows the spectra of amine 1a (1.0 mm in CH 3 CN). Red curve shows the spectra after adding 20 ul of amine 1a solution to RB (3 ml). The spectra reveals that the fluorescence of RB is quenched with the addition of tertiary amine. Figure S1 Fluorescence quenching spectra
8 S8 NMR Spectra of New Compounds
9 S9 Computational Details All DFT calculations were performed using Gaussian 09 program (Revision A.02). 1 Geometries were optimized at UM06-2X 2 /6-31+G(d,p). The optimized structures were confirmed to be true minima using vibrational frequency analysis: no imaginary frequency. Conformational sampling was performed with MacroModel. Single point calculations were perfomed on the UM06-2X/6-31+G(d,p) geometries at UM06-2X/ G(2df,2p) both in the gas phase and in nitromethane via the IEFPCM continuum model with radii and non-electrostatic terms from Truhlar and coworkers SMD solvation model. 3 Zero point correction and thermal correction to energy, enthalpy and Gibbs free energy are obtained at K, 1 atmosphere, and the most abundant isotopes. Table 1: UM06-2X/6-31+G(d,p) a result for neutral species and single point calculation at UM06-2X/ G(2df,2p)//UM06-2X/6-31+G(d,p) b Compound 1a-Conformation 1 1a-Conformation 2 1a-Conformation 3 3-Conformation 1 UM06-2X/6-31+G(d,p) a UM06-2X / G(2df,2p) b Zero Point Correction a Thermal correction to Enthalpy a Thermal correction to Gibbs Free Energy a Table 2: UM06-2X/6-31+G(d,p) a result for cationic species and single point calculation at UM06-2X/ G(2df,2p)//UM06-2X/6-31+G(d,p) b Compound 1a + -Conformation 1 1a + -Conformation 2 1a + -Conformation Conformation 1 UM06-2X/6-31+G(d,p) a UM06-2X / G(2df,2p) b Zero Point Correction a Thermal correction to Enthalpy a Thermal correction to Gibbs Free Energy a
10 S10 Table 3: SMD/UM06-2X/6-31+G(d,p) a and single point calculation at SMD/UM06-2X/ G(2df,2p)// UM06-2X/6-31+G(d,p) b result for neutral species Compound 1a-Conformation 1 1a-Conformation 2 1a-Conformation 3 3-Conformation UM06-2X/6-31+G(d,p) a UM06-2X / G(2df,2p) b Zero Point Correction a Thermal correction to Enthalpy a Thermal correction to Gibbs Free Energy a Table 4: SMD/UM06-2X/6-31+G(d,p) and single point calculation at SMD/UM06-2X/ G(2df,2p)// UM06-2X/6-31+G(d,p) result for cationic species Compound UM06-2X/6-31+G(d,p 1a + -Conformatio n 1 1a + -Conformatio n 2 1a + -Conformatio n Conformatio ) a UM06-2X / G(2df,2p) b Zero Point Correction a Thermal correction to Enthalpy a Thermal correction to Gibbs Free Energy a n 1 Table 5: SMD/UM06-2X/6-31+G(d,p) and single point calculation at SMD/UM06-2X/ G(2df,2p)// UM06-2X/6-31+G(d,p) result for Iminium Compound 1a-H + -Conformation 1 1a-H + -Conformation 2 3-H + -Conformation UM06-2X/6-31+G(d,p) a UM06-2X / G(2df,2p) b Thermal correction to Gibbs Free Energy a
11 S11 The relative stability between the iminium of 1a and 3 is obtained by ΔG 1 -ΔG 2, as the Gibbs free energy of hydrogen radical, ΔG 1 -ΔG 2 = (G 1a-H+ - G 1a+ ) (G 3-H+ - G 3+ ). Table 6: Ionization Potential, ΔG S (X + ) and ΔG S (X) Compound Ionization Potential (ev) ΔG ox,gas ΔG ox,solv 1a Definition for Table 6 For 1a in which the relative Gibbs free energies for different conformers were sufficiently close, the quantities in Table 6 are calculated as weighted averages over the conformers using the Boltzmann distribution. Ionization Potential = (E radical cation,gas + ZPE) (E neutral,gas + ZPE), where E refers to the electronic energy from UM06-2X/ G(2df,2p)//UM06-2X/6-31+G(d,p) and ZPE refers to the zero point energy at UM06-2X/6-31+G(d,p) ΔG ox,gas = G radical cation,gas G neutral,gas, where G refers to sum the electronic energy from UM06-2X/ G(2df,2p)//UM06-2X/6-31+G(d,p) and thermal correction to Gibbs free energy at UM06-2X/6-31+G(d,p) ΔG ox,solv = G radical cation,solv G neutralsolv, where G refers to sum the electronic energy from SMD-UM06-2X/ G(2df,2p)//UM06-2X/6-31+G(d,p) and thermal correction to Gibbs free energy at SMD-UM06-2X/6-31+G(d,p). Solvent being modeled is nitromethane. Standard Redox Potential Calculation Calculations were performed using a slightly modified methodology from reference Guo and co-workers 9 : Closed-shell restricted wavefunction was used for N,N-dimethylaniline and its derivatives, Unrestricted open-shell wavefunctions were used for all cationic radical of N,N-dimethylaniline and its derivatives. The B3LYP functional was used for all calculations. Geometry optimizations were performed at B3LYP/6-31+G(d). Additional single point calculations were performed at B3LYP/ G(2df,2p). Solvation free energies were obtained B3LYP/6-31+G(d,p) using the IEFPCM solvation model from B3LYP/6-31+G(d) optimized structures. Alpha=1.20 was specified in
12 S12 SCRF calculation. (Guo and coworkers used D-PCM which is not implemented in Gaussian 09) eV was used for the free energy associated with the NHE half cell. 10 It was found that experimental E 0 are systematically underestimated by calculations described above (Table 7. Uncorrected). Guo and co-workers added 0.28eV to the calculated adiabiatic ionization potential, which contributes to an improvement in their calculated E 0 when compared with the experimental E 0. Optimization of the solvation model used to calculate the solvent free energies is important, in this study we used an unoptimized IEFPCM model as implemented in Gaussian 09 with alpha=1.20 (Table 7, Ref 9*). The results for most compound is similar to those reported by Guo and coworkers (Table 7, Ref 9). By applying a simple linear regression model, the corrected E 0 can be obtained which is in excellent agreement with the experimental E 0 (table 7, Corrected). Since this is a preliminary study, a small dataset of 6 compounds (Table 7, entries 1-6) was used to train the linear regression model and no validation of the model was performed. As the compounds which we are interested to predict the E 0 are structurally similar to the compounds in the dataset, it is expected that the predicted E 0 should be fairly accurate, however, further studies would be required to affirm this. Table 7: Experimental and Calculated E 0 values in MeCN (References for experimental can be found in the supporting information of reference 9) Compound E 0 vs NHE /ev (Experimental) vs NHE E 0 vs NHE /ev /ev E 0 E 0 vs NHE /ev (Uncorrected) (Ref 9) (Ref 9*) (Corrected) E 0 /ev vs NHE N/A 0.68 N/A N/A 0.84 N/A
13 S13 Cartesian Coordinates 1a-conformation 1 gas phase C C C C C H H C C H H C C H H H H H H N C C C C H C H C H H H a-conformation 2 gas phase C C C C C
14 S14 H H C C H H C C H H H H H H N C C C C H C H C H H H a-conformation 3 gas phase C C C C C H H C C H H C C H H
15 S15 H H H H N C C C C H C H C H H H a-conformation 1 scrf=(smd,solvent=nitromethane) C C C C C H H C C H H C C H H H H H H N C C C C H
16 S16 C H C H H H a-conformation 2 scrf=(smd,solvent=nitromethane) C C C C C H H C C H H C C H H H H H H N C C C C H C H C H H H a-conformation 3 scrf=(smd,solvent=nitromethane) C
17 S17 C C C C H H C C H H C C H H H H H H N C C C C H C H C H H H conformation 1 gas phase C C C C C C H H H H N
18 S18 C H H H C H H H C H H H conformation 1 scrf=(smd,solvent=nitromethane) C C C C C C H H H H N C H H H C H H H C H H H a + -conformation 1 gas phase C C C
19 S19 C C H H C C H H C C H H H H H H N C C C C H C H C H H H a + -conformation 2 gas phase C C C C C H H C C H H C C
20 S20 H H H H H H N C C C C H C H C H H H a + -conformation 3 gas phase C C C C C H H C C H H C C H H H H H H N C C C
21 S21 C H C H C H H H a + -conformation 1 scrf=(smd,solvent=nitromethane) C C C C C H H C C H H C C H H H H H H N C C C C H C H C H H H a + -conformation 2 scrf=(smd,solvent=nitromethane)
22 S22 C C C C C H H C C H H C C H H H H H H N C C C C H C H C H H H a + -conformation 3 scrf=(smd,solvent=nitromethane) C C C C C H H C C
23 S23 H H C C H H H H H H N C C C C H C H C H H H a + -conformation 1 gas phase C C C C C C H H H H N C H H H C H H H
24 S24 C H H H a + -conformation 1 scrf=(smd,solvent=nitromethane) C C C C C C H H H H N C H H H C H H H C H H H a-H + -conformation 1 scrf=(smd,solvent=nitromethane) C C C C C H C C H H C
25 S25 C H H H H H H N C C C C H C H C H H H a-H + -conformation 2 scrf=(smd,solvent=nitromethane) C C C C C H C C H H C C H H H H H H N C C C
26 S26 C H C H C H H H H + -conformation 1 scrf=(smd,solvent=nitromethane) C C C C C C H H H H N C H H C H H H C H H H Table 7 Entry 1 RB3LYP/6-31+G(d) C C C C C C H H
27 S27 H H H N C H H H C H H H Table 7 Entry 1 RB3LYP/6-31+G(d) cationic radical C C C C C C H H H H N C H H H C H H H H Table 7 Entry 2 RB3LYP/6-31+G(d) C C C C C C
28 S28 H H H H N C H H H C H H H N C H H H C H H H Table 7 Entry 2 RB3LYP/6-31+G(d) cationic radical C C C C C C H H H H N C H H H C H H H
29 S29 N C H H H C H H H Table 7 Entry 3 RB3LYP/6-31+G(d) C C C C C C H H H N C H H H C H H H H N C H H H C H H H Table 7 Entry 3 RB3LYP/6-31+G(d) cationic radical C
30 S30 C C C C C H H H N C H H H C H H H H N C H H H C H H H Table 7 Entry 4 RB3LYP/6-31+G(d) C C C C C C H H H N C H H H
31 S31 C H H H H N C H H H C H H H Table 7 Entry 4 RB3LYP/6-31+G(d) cationic radical C C C C C C H H H N C H H H C H H H H N C H H H C H H
32 S32 H Table 7 Entry 5 RB3LYP/6-31+G(d) C C C C C C H H H H N C H H H C H H H C H H H O Table 7 Entry 5 RB3LYP/6-31+G(d) cationic radical C C C C C C H H H H N C H
33 S33 H H C H H H O C H H H Table 7 Entry 6 RB3LYP/6-31+G(d) C C C C C C H H H H N C H H H C H H H N O O Table 7 Entry 6 RB3LYP/6-31+G(d) cationic radical C C C C C
34 S34 C H H H H N C H H H C H H H H Table 7 Entry 7 RB3LYP/6-31+G(d) C C C C C C H H H H N C H H H C H H H C H H H Table 7 Entry 7 RB3LYP/6-31+G(d) cationic radical
35 S35 C C C C C C H H H H N C H H H C H H H C H H H Table 7 Entry 8 RB3LYP/6-31+G(d) Conformation 1 C C C C C H H C C H H C C H H H H H
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
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
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
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
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
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
Supporting Information. DBU-Mediated Metal-Free Oxidative Cyanation of α-amino. Carbonyl Compounds: Using Molecular Oxygen as the Oxidant
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
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
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
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
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
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
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
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
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](/thumbs/85/92425281.jpg "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]
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,
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
Trisulfur Radical Anion as the Key Intermediate for the. Synthesis of Thiophene via the Interaction between Elemental.
Trisulfur Radical Anion as the Key Intermediate for the Synthesis of Thiophene via the Interaction between Elemental Sulfur and NaOtBu Guoting Zhang, a Hong Yi, a Hong Chen, a Changliang Bian a Chao Liu
Supporting information. An improved photo-induced fluorogenic alkene-tetrazole reaction for protein labeling
Supporting information An improved photo-induced fluorogenic alkene-tetrazole reaction for protein labeling X. Shang, 1 R. Lai, 1,3 X. Song, 1 H. Li, 1,3 W. Niu, 2 and J. Guo 1 * 1. Department of Chemistry,
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,
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:
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,*
SUPPORTING INFORMATION. A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on Distyryl-Bodipy Fluorophore
SUPPORTING INFORMATION A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on Distyryl-Bodipy Fluorophore Serdar Atilgan,, Tugba Ozdemir, and Engin U. Akkaya * Department
Supporting Information
Supporting Information Eosin Y Catalyzed Visible Light xidative C-C and C-P bond Formation Durga Prasad Hari, Burkhard König* Institut für rganische Chemie, Universität Regensburg, Universitätsstraße 31,
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,
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,
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,
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,
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
SUPPORTING INFORMATION
Dynamic covalent templated-synthesis of [c2]daisy chains. Altan Bozdemir, a Gokhan Barin, a Matthew E. Belowich, a Ashish. Basuray, a Florian Beuerle, a and J. Fraser Stoddart* ab a b Department of Chemistry,
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
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:
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
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,
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,
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,
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
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,*
Supporting information. Enantioselective synthesis of 2-methyl indoline by palladium catalysed asymmetric C(sp 3 )-H activation/cyclisation.
Supporting information Enantioselective synthesis of 2-methyl indoline by palladium catalysed asymmetric C(sp 3 )-H activation/cyclisation Saithalavi Anas, Alex Cordi and Henri B. Kagan * Institut de Chimie
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
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,
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
Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle
Supporting Information Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Liu-Pan Yang, a,b Fei Jia, a Jie-Shun Cui, a Song-Bo Lu, a and Wei Jiang* a a Department of Chemistry, South
Supporting Information
Supporting Information Wiley-VCH 25 69451 Weinheim, Germany Direct Asymmetric α-fluorination of Aldehydes [**] Derek D. Steiner, Nobuyuki Mase, Carlos F. Barbas III* [*] Prof. Dr. C. F. Barbas III, Derek
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
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
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
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,*
Iridium-catalyzed regioselective decarboxylative allylation of. β-ketoacids: efficient construction of γ, δ-unsaturated ketones
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Iridium-catalyzed regioselective decarboxylative allylation of β-ketoacids: efficient construction
Supporting Information
Gold(I) Catalyzed Intra and Intermolecular Alkenylations of β Yne Pyrroles: Facile Formation of Fused Cycloheptapyrroles and Functionalized Pyrroles Bin Pan, Xiaodong Lu, Chunxiang Wang, Yancheng Hu, Fan
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
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,
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,
Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe
Supporting Information for Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Ho Yu Au-Yeung, Jefferson Chan, Teera Chantarojsiri and Christopher J. Chang* Departments
Qile Wang, and Nan Zheng* Department of Chemistry and Biochemistry, University of Arkansas. Fayetteville, Arkansas,
Supporting Information A Photocatalyzed Synthesis of Naphthalenes by Using Aniline as a Traceless Directing Group in [4+2] Annulation of AminoBenzocyclobutenes with Alkynes Qile Wang, and Nan Zheng* Department
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
Rational design of a ratiometric fluorescent probe with a large emission shift for the facile detection of Hg 2+
Rational design of a ratiometric fluorescent probe with a large emission shift for the facile detection of Hg 2+ Weimin Xuan, a Chen Chen, b Yanting Cao, a Wenhan He, a Wei Jiang, a Kejian Li, b* and Wei
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,
Asymmetric Michael Addition of -Fluoro- -nitroalkanes to Nitroolefins: Facile Preparation of Fluorinated Amines and Tetrahydropyrimidines
Electronic Supplementary Material (ESI) for Chemical Communications. This journal is The Royal Society of Chemistry 2014 Asymmetric Michael Addition of -Fluoro- -nitroalkanes to Nitroolefins: Facile Preparation
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
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:
Supporting Information
Supporting Information Efficient Short Step Synthesis of Corey s Tamiflu Intermediate Nsiama Tienabe Kipassa, Hiroaki kamura, * Kengo Kina, Tetsuo Iwagawa, and Toshiyuki Hamada Department of Chemistry
Supporting Information for
Supporting Information for Unusual reactions of diazocarbonyl compounds with α,βunsaturated δ-amino esters: Rh(II)-catalyzed Wolff rearrangement and oxidative cleavage of N H-insertion products Valerij
Supporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 214 Supporting Information Rapid and sensitive detection of acrylic acid using a novel fluorescence
Protodecarboxylation of benzoic acids under radical conditions. Supporting Information
Protodecarboxylation of benzoic acids under radical conditions Sangwon Seo, a John B. Taylor b and Michael F. Greaney a * a School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL,UK
Tuning Porosity and Activity of Microporous Polymer Network Organocatalysts by Co-Polymerisation
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Tuning Porosity and Activity of Microporous Polymer Network Organocatalysts
Supporting Information
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2017 Supporting Information Direct copper-catalyzed oxidative trifluoromethylthiolation
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
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
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
Electronic Supplementary Information for. A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective
Electronic Supplementary Information for A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective and Sensitive Detection of H 2 S: Synthesis, Spectra and Bioimaging Changyu Zhang, 1 Runyu Wang,
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,
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
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
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,
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
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,
Supporting Information - I: Experimental Procedures and Characterization
Supporting Information - I: Experimental Procedures and Characterization The Direct Reductive Amination of Electron-deficient Amines with Aldehydes: the Unique Reactivity of Re 2 O 7 Catalyst 1 Braja Gopal
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.
Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain
rganic Lett. (Supporting Information) 1 Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain Charles Kim, Richard Hoang and Emmanuel A. Theodorakis* Department of Chemistry
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
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
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
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,
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
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*,,
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
Supporting Information
Supporting Information Nano CuFe 2 O 4 as a Magnetically Separable and Reusable Catalyst for the Synthesis of Diaryl / Aryl Alkyl Sulfides via Cross-Coupling Process under Ligand Free Conditions Kokkirala
Supplementary Table S1: Response evaluation of FDA- approved drugs
SUPPLEMENTARY DATA, FIGURES AND TABLE BIOLOGICAL DATA Spheroids MARY-X size distribution, morphology and drug screening data Supplementary Figure S1: Spheroids MARY-X size distribution. Spheroid size was
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
Regioselective Silylation of Pyranosides Using a Boronic Acid / Lewis Base Co-Catalyst System
Regioselective Silylation of Pyranosides Using a Boronic Acid / Lewis Base Co-Catalyst System Doris Lee and Mark S. Taylor* Department of Chemistry, Lash Miller Laboratories, University of Toronto 80 St.
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](/thumbs/84/89552735.jpg "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
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:
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
Copper-Catalyzed Oxidative Cyclization of Carboxylic Acids
Copper-Catalyzed xidative Cyclization of Carboxylic Acids Supplementary material (51 pages) Shyam Sathyamoorthi and J. Du Bois * Department of Chemistry Stanford University Stanford, CA 94305-5080 General.
A Combination of Visible-light Photoredox and Metal Catalysis for the Mannich-type Reaction of N-Aryl Glycine Esters
A Combination of Visible-light Photoredox and Metal Catalysis for the Mannich-type Reaction of -Aryl Glycine Esters Izumi kamura, 1 Soyoung Park,* 1 Ji Hoon Han, 1 Shunta otsu, 3 and Hiroshi Sugiyama*
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
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
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
Asymmetric Michael Addition Reactions of Nitroalkanes to 2-Furanones Catalyzed by Bifunctional Thiourea catalysts
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 25 Asymmetric Michael Addition Reactions of Nitroalkanes to 2-Furanones Catalyzed