A New Type of Bis(sulfonamide)-Diamine Ligand for a Cu(OTf) 2 -Catalyzed Asymmetric Friedel-Crafts Alkylation Reaction of Indoles with Nitroalkenes
|
|
|
- Ἑλένη Παπάγος
- 5 χρόνια πριν
- Προβολές:
Transcript
1 A ew Type of Bis(sulfonamide)-Diamine Ligand for a Cu(OTf) 2 -Catalyzed Asymmetric Friedel-Crafts Alkylation Reaction of Indoles with itroalkenes Jing Wu, Xincheng Li, Fan Wu, and Boshun Wan* Dalian Institute of Chemical ysics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian , China. bswan@dicp.ac.cn Supporting Information
2 Table of Contents 1. General information S2 2. The preparation of Bis(sulfonamide)-Diamine Ligand L1 L7 S2 3. Optimization of the model reaction S2 S3 4. Asymmetric Friedel-Craft Alkylation of indole with nitroalkene S3 5. Results of some commercially available indole analogues S3-S4 6. Analysis of the ligand L1-L7 and products S3 S10 7. Copy of MR, RMS and PLC for racemic and chiral compounds S11 S65 S1
3 1. General information All reactions were carried out under an atmosphere of argon using standard Schlenk techniques, unless otherwise noted. 1 MR and 13 C MR spectra were recorded on Bruker DRX 400 or Bruker DRX 500 spectrometers (400 Mz or 500 Mz for 1 MR, 100 Mz or 126 Mz for 13 C MR, see details of each compound) using CDCl 3 or CD 3 COCD 3 as solvent. Tetramethylsilane (δ = 0) or CDCl 3 (δ = 7.27) or CD 3 COCD 3 (2.05 ppm) serves as the internal standard for 1 MR and CDCl 3 (77.16 ppm) and CD 3 COCD 3 (29.84 ppm) for 13 C MR. Coupling constants (J) are reported in z and refer to apparent peak multiplications. Optical rotations were measured with JASCO P 1010 polarimeter. RMS data were obtained with Micromass PLC-Q-TOF mass spectrometer Flash column chromatography was performed on silica gel ( mesh). TLC analysis was performed using glass-backed plates coated with 0.2 mm silica. Commercially available reagents were used throughout without further purification. All solvents were purified according to the standard procedures. 2. The preparation of Bis(sulfonamide)-Diamine Ligand L1 L7 R 1 R 1 O R 2 TsCl, K 2 CO 3 2 C 3 C Ts R 2 1,2-diamines, reflux C 3 C or C 3 O R 2 Ts Ts R 2 L1-L7 were synthesized by the same procedure in the literature 1,2,3. 3. Optimization of model reaction Table 1. Screening of Lewis acids for the reaction Entry Metal salt Yield (%) Ee (%) 1 Cu(OTf) FeCl Ag(OTf) Zn(OTf) Cu(OTf). C CuCl Cu(OAc) Jin, W.; Li, X. C.; uang, Y. B.; Wu, F.; Wan, B. S. Chem. Eur. J. 2010, 16, Jin, W.; Li, X. C.; Wan, B. S. J. Org. Chem. 2011, 76, Pei, Y.; Brule, E.; Moberg, C. Org. Biomol. Chem. 2006, 4, 544. S2
4 Table 2. Optimization of the solvents Entry Solvent Isolated yield (%) Ee (%) 1 toluene C 2 Cl CCl DCE Et 2 O TF C 3 C p-xylene CF benzene Asymmetric 1,4-addition of arylboronic acids to 2-cyclohexenone Under argon atmosphere, a mixture of Cu(OTf) 2 (4.5 mg, mmol) and L6 (9.5 mg, mmol) in CF 3 (3 ml) was stirred at room temperature in a 25 ml Schlenk tube for 2 h to give the catalyst. After putting it into a freezer with the temperature of 0 C, this mixture was added nitroalkene (0.375 mmol). After stirred for 10 min, indole (0.25 mmol) was added. The reaction was stirred at 0 C and monitored by TLC. When the reaction was over, the reaction mixture was directly charged onto a column (silica gel) and flash chromatograph with a mixture of petroleum ether/c 3 CO 2 Et to afford the product. 5. Results of some commercially available indole analogues S3
5 Entry R Yield (%) Ee (%) 1 1-Me Me Me Analysis of the ligand L1-L7 and product L1 white solid; m.p. = C; yield 92%; R f = 0.33 Ts Ts (C 2 Cl 2 /C 3 O = 30/1); [α] 23 D = (c 0.63, CCl 3 ); MR (500 Mz, CDCl 3 ) δ 7.81 (d, J = 8.3 z, 4), 7.29 (d, J = 8.0 z, 4), (m, 6), (m, 4), 5.78 (s, 2), 3.52 (s, 2), (m, 2), 2.54 (dd, J = 12.6, 5.0 z, 2), (m, 9), (m, 1), 0.68 (d, J = 6.7 z, 6), 0.64 (d, J = 6.8 z, 6); 13 C MR (126 Mz, CDCl 3 ) δ 143.0, 141.5, 139.0, 129.6, 128.0, 127.9, 127.1, 126.9, 69.0, 60.0, 48.0, 30..0, 21.6, 19.4, 18.9; RMS Calculated for C O 4 S 2 [M+] , found Ts Ts L2 white solid; m.p. = C; yield 83%; R f = 0.40 (C 2 Cl 2 /C 3 O = 30/1); [α] 25 D = (c 0.75, CCl 3 );. 1 MR (500 Mz, CDCl 3 ) δ 7.68 (d, J = 8.1 z, 4), 7.20 (d, J = 8.1 z, 4), (m, 6), 6.97 (d, J = 6.4 z, 4), 5.56 (s, 2), 3.49 (s, 2), 3.14 (s, 2), 2.46 (dd, J = 11.6, 7.2 z, 2), (m, 8), (m, 3), 0.73 (d, J = 6.8 z, 6), 0.68 (d, J = 6.8 z, 6). 13 C MR (126 Mz, CDCl 3 ) δ 142.9, 141.4, 139.0, 129.6, 128.1, 128.0, 127.0, 69.4, 60.0, 48.5, 30.7, 21.6, 19.2, 18.6; RMS Calculated for C O 4 S 2 [M+] , found Ts L3: known compond 3 white foam; m.p. = C; yield 80%; R f = 0.35 (C 2 Cl 2 /C 3 O = 30/1); [α] 25 D = 12.3 (c 1.09, CCl 3 ); 1 MR (400 Mz, CDCl 3 ) δ 7.81 (d, J = 8.2 z, 4), 7.28 (d, J = 8.1 z, 4), 5.83 (s, 1), (m, 2), 2.87 Ts (dd, J = 12.1, 5.0 z, 2), 2.59 (dd, J = 12.1, 3.5 z, 2), 2.41 (s, 6), (m, 2), 1.99 (d, J = 12.4 z, 2), 1.73 (m, 4), (m, 2), 1.02 (dd, J = 13.1, 6.1 z, 2), 0.76 (d, J = 6.7 z, 6), 0.67 (d, J = 6.7 z, 6); 13 C MR (101 Mz, CDCl 3 ) δ 142.9, 138.8, 129.6, 127.0, 61.4, 60.2, 47.4, 32.1, 29.9, 25.3, 21.6, 19.4, Ts Ts L4: white foam; m.p. = C; yield 79%; R f = 0.23 (C 2 Cl 2 /C 3 O = 30/1); [α] 25 D = (c 1.28, CCl 3 ); 1 MR (500 Mz, CDCl 3 ) δ 7.83 (d, J = 8.3 z, 4), 7.30 (d, J = 8.2 z, 4), (m, 6), 6.92 (dd, J = 7.6, 1.6 z, 4), 5.66 (s, 2), 3.53 (s, 2), 3.48 (m, 2), 2.55 (s, 2), (m, 8), 2.34 (dd, J = 12.8, 7.1 z, 2), 0.92 (d, J = 6.6 z, 6); 13 C MR (126 Mz, CDCl 3 ) δ 143.1, 141.1, 138.7, 129.7, 128.0, 127.2, 127.0, 68.0, 51.8, 48.9, 21.6, 19.1; RMS Calculated for C O 4 S 2 [M+] , found S4
6 L5: white solid; m.p. = C; yield 95%; R f = 0.30 (C 2 Cl 2 /C 3 O = 30/1); [α] 25 D = (c 1.25, CCl 3 ); 1 MR (400 Mz, CDCl 3 ) δ 7.60 (d, J = 8.2 z, 4), 7.15 (d, J Bn Bn = 8.1 z, 4), (m, 12), 6.93 (m, 8), 5.71 (s, 2), Ts Ts (m, 4), 2.74 (dd, J = 13.8, 7.3 z, 2), (m, 4), 2.48 (dd, J = 12.4, 4.4 z, 3), 2.39 (s, 6); 13 C MR (101 Mz, CDCl 3 ) δ 142.9, 141.3, 138.2, 137.7, 129.7, 129.3, 128.5, 128.1, 128.0, 127.0, 127.0, 126.4, 69.2, 55.3, 50.3, 39.2, 21.7; RMS Calculated for C O 4 S 2 [M+] , found L6: white foam; m.p. = C; yield 55%; R f = 0.68 (C 2 Cl 2 /C 3 O = 30/1); [α] 25 D = (c 1.26, CCl 3 ); 1 MR (400 Mz, CDCl 3 ) δ 7.81 (d, J = 8.3 z, 4), 7.33 (d, J = 8.1 z, 4), (m, 10), (m, 6), 6.96 Ts Ts (dd, J = 6.5, 3.0 z, 4), 5.73 (s, 2), 3.95 (t, J = 5.4 z, 2), 3.90 (s, 2), 3.49 (dd, J = 13.0, 4.6 z, 2), 3.12 (dd, J = 13.0, 6.4 z, 2), 2.96 (s, 1), 2.49 (s, 6); 13 C MR (101 Mz, CDCl 3 ) δ 143.3, 141.4, 141.3, 137.3, 129.8, 128.5, 127.9, 127.9, 127.4, 127.1, 127.1, 126.9, 67.4, 60.3, 47.6, 21.6; RMS Calculated for C O 4 S 2 [M+] , found Ts Ts L7: white solid, m.p. = C; yield 83%; R f = 0.48 (C 2 Cl 2 /C 3 O = 30/1); [α] 25 D = 30.9 (c 1.04, CCl 3 ); MR (400 Mz, CDCl 3 ) δ 7.77 (d, J = 7.8 z, 4), 7.27 (d, J = 7.9 z, 4), 7.13 (m, 6), 6.97 (d, J = 7.1 z, 4), 5.74 (s, 2), 3.48 (s, 2), 3.14 (s, 2), 2.55 (dd, J = 12.9, 4.4 z, 2), 2.42 (s, 8), 2.26 (dd, J = 12.8, 3.8 z, 2), 0.74 (s, 18); 13 C MR (101 Mz, CDCl 3 ) δ 142.8, 141.5, 139.1, 129.5, 128.0, 127.9, 127.1, 127.0, 69.0, 61.8, 47.0, 34.8, 27.4, 21.6; RMS Calculated for C O 4 S 2 [M+] , found a (R)-(2-itro-1-phenylethyl)-1-indole: known compound 4 ; Following the general procedure, the compond was obtained as yellow oil in 99% yield and 95% ee; [α] 22 D = 22.3 (c 0.91, C 2 Cl 2 ); [lit. 5 : [α] 20 D = 24.9 (c O 1.06, C 2 Cl 2 ) for 96% ee;] R f = 0.3 (petroleum ether/etoac = 4/1); 1 2 MR (500 Mz, CDCl 3 ) δ 8.05 (s, 1), 7.44 (dd, J = 8.0, 0.7 z, 1), (m, 6), (m, 1), 7.07 (m, 1), 7.02 (dd, J = 2.4, 0.5 z, 1), 5.18 (t, J = 8.0 z, 1), 5.06 (dd, J = 12.5, 7.6 z, 1), 4.94 (dd, J = 12.5, 8.3 z, 1); 13 C MR (126 Mz, CDCl 3 ) δ 139.4, 136.7, 129.1, 127.9, 127.7, 126.3, 122.9, 121.7, 120.1, 119.1, 114.7, 111.5, 79.7, 41.7; PLC: Daicel Chiralpak AD-, hexane/i-pro = 90/10, Flow rate = 1.0 ml/min, UV = 210 nm, t R = 25.2 min (major) and t R = 27.7 min. 4 Jia, Y. X.; Zhu, S. F.; Yang, Y.; Zhou, Q. L. J. Org. Chem. 2006, 71, 75. S5
7 Cl 3b (R)-3-[1-(4-Chlorophenyl)-2-nitroethyl]-1-indole: known compound 4 ; yellow oil; 96% yield; 92% ee; [α] 23 D = 8.34 (c 2.11, C 2 Cl 2 ); [lit. 5 : [α] 20 D = 9.7 (c 0.79, C 2 Cl 2 ) for 91% ee;] R f = 0.28 O (petroleum ether/etoac = 4/1); 1 2 MR (400 Mz, Acetone) δ (s, 1), 7.52 (d, J = 8.0 z, 1), (m, 2), 7.42 (m, 2), (m, 2), (m, 1), (m, 1), (m, 3); 13 C MR (101 Mz, Acetone) δ 140.4, 137.7, 133.2, 130.6, 129.4, 127.1, 123.0, 122.8, 120.0, 119.4, 114.4, 112.4, 79.9, 41.6; PLC: Daicel Chiralcel OD- column, hexane/i-pro = 70/30, Flow rate = 1.0 ml/min, UV = 254 nm, t R = 25.6 min and t R = 34.1 min (major). Cl 3c (R)-3-[1-(3-Chlorophenyl)-2-nitroethyl]-1-indole: known compound 5 ; yellow oil; 94% yield; 94% ee; [α] 23 D = (c 1.62, C 2 Cl 2 ); [lit. 5 : [α] 20 D = 18.1 (c 1.06, C 2 Cl 2 ) for 92% ee;] R f = 0.3 O (petroleum ether/etoac = 4/1); 1 2 MR (500 Mz, CDCl 3 ) δ 8.09 (s, 1), 7.42 (dd, J = 8.0, 0.8 z, 1), (m, 1), 7.30 (d, J = 2.2 z, 1), (m, 4), 7.08 (ddd, J = 8.0, 7.1, 0.9 z, 1), 7.01 (dd, J = 2.5, 0.6 z, 1), 5.15 (t, J = 8.0 z, 1), 5.03 (dd, J = 12.7, 7.5 z, 1), 4.90 (dd, J = 12.7, 8.4 z, 1); 13 C MR (126 Mz, CDCl 3 ) δ 141.5, 136.7, 135.0, 130.3, 128.1, 128.0, 126.1, 126.1, 123.0, 121.7, 120.3, 118.9, 113.9, 111.6, 79.3, 41.3; PLC: Daicel Chiralcel OD- column, hexane/i-pro = 70/30, Flow rate = 1.0 ml/min, UV = 254 nm, t R = 24.9 min and t R = 38.4 min (major). 3d (R)-3-[1-(2-Chlorophenyl)-2-nitroethyl]-1-indole: known Cl compound 4, yellow oil; 99% yield; 97% ee; [α] 21 D = 80.9 (c 1.51, C 2 Cl 2 ); [lit. 5 : [α] 20 D = 82.7 (c 1.12, C 2 Cl 2 ) for 91% ee;] R f = 0.28 O (petroleum ether/etoac = 4/1); 1 2 MR (400 Mz, Acetone) δ (s, 1), 7.55 (d, J = 7.9 z, 1), (m, 1), (m, 1), 7.42 (m, 2), (m, 2), (m, 1), (m, 1), 5.77 (t, J = 8.0 z, 1), 5.30 (dd, J = 13.2, 8.3 z, 1), 5.22 (dd, J = 13.2, 7.8 z, 1); 13 C MR (101 Mz, Acetone) δ 138.5, 137.7, 134.3, 130.6, 130.1, 129.6, 128.3, 127.3, 123.7, 122.8, 120.1, 119.2, 113.6, 112.5, 78.7, 38.5; PLC: Daicel Chiralcel OD- column, hexane/i-pro = 70/30, Flow rate = 1.0 ml/min, UV = 254 nm, t R = 16.6 min (major) and t R = 28.5 min. 3e (R)-3-[1-(4-Methylphenyl)-2-nitroethyl]-1-indole: known compound 5, yellow oil; 99% yield; 93% ee; [α] 23 D = 15.3 (c 2.10, C 2 Cl 2 ); [lit. 5 : [α] 20 D = (c 0.83, C 2 Cl 2 ) for 96% ee;] R f = 0.25 O (petroleum ether/etoac = 4/1); 1 MR (400 Mz, Acetone) δ (s, 2 1), 7.52 (d, J = 7.9 z, 1), 7.40 (d, J = 8.2 z, 1), 7.36 (m, 3), 7.10 (m, 3), (m, 1), 5.27 (dd, J = 15.6, 10.8 z, 1), (m, 2), 2.26 (s, 3); 13 C MR (101 Mz, Acetone) δ 138.4, 137.8, 137.4, 130.0, 128.7, 127.3, 122.8, 122.6, 119.9, 119.5, 115.0, 112.3, 80.3, 42.0, PLC: 5 Guo, F. F. Lai, G. Y.; Xiong, S. S.; Wang, S. J.; Wang, Z. Y. Chem. Eur. J. 2010, 16, S6
8 Daicel Chiralcel OD- column, hexane/i-pro = 70/30, Flow rate = 1.0 ml/min, UV = 254 nm, t R = 17.9 min and t R = 22.2 min (major). MeO 3f (R)-3-[1-(4-Methoxyphenyl)-2-nitroethyl]-1-indole: known compound 4, white solid; m.p o C; 99% yield; 88% ee; [α] 23 D = (c 2.22, C 2 Cl 2 ); [lit. 5 : [α] 20 D = 28.2 (c 1.04, C 2 Cl 2 ) for 95% ee;] R f = 0.15 (petroleum ether/etoac = 4/1); 1 MR (500 Mz, O 2 CDCl 3 ) δ 8.05 (s, 1), 7.43 (dd, J = 8.0, 0.7 z, 1), 7.34 (d, J = 8.2 z, 1), (m, 2), 7.19 (ddd, J = 8.2, 7.2, 1.0 z, 1), 7.07 (ddd, J = 8.0, 7.1, 1.0 z, 1), 7.00 (dd, J = 2.5, 0.7 z, 1), (m, 2), 5.13 (t, J = 8.0 z, 1), 5.03 (dd, J = 12.3, 7.5 z, 1), 4.89 (dd, J = 12.3, 8.4 z, 1), 3.76 (s, 3); 13 C MR (126 Mz, CDCl 3 ) δ 159.1, 136.7, 131.4, 129.0, 126.3, 122.8, 121.6, 120.1, 119.2, 115.0, 114.5, 111.5, 79.9, 55.4, 41.0; PLC: Daicel Chiralcel OD- column, hexane/i-pro = 70/30, Flow rate = 1.0 ml/min, UV = 254 nm, t R = 24.8 min and t R = 30.3 min (major). OMe 3g (R)-3-[1-(2-Methoxyphenyl)-2-nitroethyl]-1-indole: known compound 4 ; yellow oil; 96% yield; 93% ee; [α] 21 D = 48.3 (c 1.87, C 2 Cl 2 ); [lit. 5 : [α] 20 D = 47.8 (c 1.15, C 2 Cl 2 ) for 95% ee;] R f = 0.3 O 2 (petroleum ether/etoac = 4/1); 1 MR (400 Mz, Acetone) δ (s, 1), 7.52 (d, J = 7.9 z, 1), (m, 2), (m, 2), (m, 1), (m, 2), 6.85 m, 1), 5.64 (t, J = 8.0 z, 1), 5.18 (dd, J = 8.0, 1.2 z, 2), 3.93 (s, 3); 13 C MR (101 Mz, Acetone) δ 157.9, 137.7, 129.6, 129.2, 129.0, 127.7, 123.4, 122.7, 121.4, 119.8, 119.5, 114.4, 112.3, 111.9, 79.0, 56.0, 35.8; PLC: Daicel Chiralcel OD- column, hexane/i-pro = 70/30, Flow rate = 1.0 ml/min, UV = 254 nm, t R = 13.7 min (major) and t R = 15.7 min. Br 3h (R)-3-[1-(2-Bromophenyl)-2-nitroethyl]-1-indole: known compound 6 ; yellow oil; 97% yield; 96% ee; [α] 22 D = 99.9 (c 1.3, C 2 Cl 2 ); R f = 0.25 (petroleum ether/etoac = 4/1); 1 MR (400 Mz, CDCl 3 ) δ O (s, 1), 7.64 (d, J = 7.8 z, 1), 7.44 (d, J = 7.9 z, 1), 7.35 (d, J = 8.2 z, 1), (m, 3), (m, 3), (m, 1), (m, 2); 13 C MR (126 Mz, CDCl 3 ) δ 138.2, 136.6, 133.6, 129.2, 128.0, 126.3, 124.6, 122.8, 122.1, 120.1, 119.1, 113.4, 111.5, 77.9, 40.7; PLC: Daicel Chiralcel OD- column, hexane/i-pro = 70/30, Flow rate = 1.0 ml/min, UV = 254 nm, t R = 30.8 min and t R = 17.5 min (major). Br O 2 3i (R)-3-[1-(3-Bromophenyl)-2-nitroethyl]-1-indole: known compound 4 ; yellow oil; 99% yield; 93% ee; [α] 22 D = 12.8 (c 2.0, C 2 Cl 2 ); [lit. 4 : [α] 20 D = (c 1.3, C 2 Cl 2 ) for 86% ee;] R f = 0.23 (petroleum ether/etoac = 4/1); 1 MR (500 Mz, CDCl 3 ) δ 8.09 (s, 1), 7.46 (t, J = 1.8 z, 1), 7.42 (dd, J = 8.0, 0.7 z, 1), 7.38 (m, 1), 7.34 (d, J = 6 Lin, S. Z.; You, T. P. Tetrahedron 2009, 65, S7
9 8.2 z, 1), (m, 3), 7.08 (m 1), 7.00 (dd, J = 2.5, 0.6 z, 1), 5.13 (d, J = 8.0 z, 1), 5.02 (dd, J = 12.7, 7.5 z, 1), 4.89 (dd, J = 12.7, 8.4 z, 1); 13 C MR (126 Mz, CDCl 3 ) δ 141.8, 136.6, 131.0, 130.9, 130.6, 126.6, 126.1, 123.2, 123.0, 121.7, 120.3, 118.9, 113.9, 111.6, 79.3, 41.3; Daicel Chiralcel OD- column, hexane/i-pro = 70/30, Flow rate = 1.0 ml/min, UV = 254 nm, t R = 25.5 min and t R = 39.2 min (major). 3j (R)-3-[1-(4-Bromophenyl)-2-nitroethyl]-1-indole: known Br compound 4 : yellow oil; 96% yield; 92% ee; [α] 25 D = +9.8 (c 1.85, C 2 Cl 2 ); [lit. 4 : [α] 20 D = 1.7 (c 1.0, C 2 Cl 2 ) for 90% ee;] R f = 0.28 (petroleum ether/etoac = 4/1); 1 MR (400 Mz, Acetone) δ O 2 (s, 1), (m, 3), 7.41 (m, 4), 7.13 (t, J = 7.6 z, 1), 7.01 (t, J = 7.5 z, 1), (m, 3); 13 C MR (101 Mz, Acetone) δ 140.9, 137.7, 132.4, 130.9, 127.1, , 121.3, 120.0, 119.4, 114.3, 112.4, 79.8, 41.7; Daicel Chiralcel OD- column, hexane/i-pro = 70/30, Flow rate = 1.0 ml/min, UV = 254 nm, t R = 27.4 min and t R = 37.4 min (major). F 3k (R)-3-[1-(2-Fluorophenyl)-2-nitroethyl]-1-indole: yellow oil, 98% yield; 96% ee; [α] 22 D = +4.4 (c 2.3, C 2 Cl 2 ); R f = 0.3 (petroleum ether/etoac = 8/1); 1 MR (400 Mz, Acetone) δ (s, 1), 7.60 (d, O 2 J = 8.0 z, 1), (m, 3), 7.28 (m, 1), (m, 3), (m, 1), 5.56 (t, J = 8.1 z, 1), 5.31 (m, 2); 13 C MR (101 Mz, Acetone) δ (d, J C-F = z), 137.6, (d, J C-F = 3.9 z), (d, J C-F = 8.5 z), (d, J C-F = 13.9 z), 127.2, (d, J C-F = 3.5 z), (d, J C-F = 1.3 z), 122.8, 120.1, 119.1, (d, J C-F = 22.5 z), 113.5, 112.5, 78.7 (d, J C-F = 1.8 z), 35.3 (d, J C-F = 3.3 z); PLC: Daicel Chiralpak AD-, hexane/i-pro = 90/10, Flow rate = 1.0 ml/min, UV = 210 nm, t R = 20.4 min (major) and t R = 28.0 min; RMS Calculated for C O 2 F [M-] , found CF 3 3l 3-[1-(3-trifluoromethylphenyl)-2-nitroethyl]-1-indole: yellow oil; 99% yield; 94% ee; [α] 21 D = 5.7 (c 0.76, C 2 Cl 2 ); R f = 0.23 (petroleum ether/etoac = 4/1); 1 MR (500 Mz, CDCl 3 ) δ 8.13 (s, 1), 7.62 (s, 1), 7.55 (d, J = 8.2 z, 2), 7.38 (d, J = 8.2 z, 1), (m, 1), O (m, 1), 7.03 (d, J = 2.1 z, 1), 5.27 (t, J = 8.0 z, 1), 5.09 (dd, J = 12.8, 7.4 z, 1), 4.96 (dd, J = 12.8, 8.5 z, 1); 13 C MR (126 Mz, CDCl 3 ) δ , , (d, J C-F = 32.8 z), , , (d, J C-F = 3.8 z), (d, J C-F = z), , , , , , , 79.08, 41.32; Daicel Chiralpak AD-, hexane/i-pro = 80/20, Flow rate = 1.0 ml/min, UV = 220 nm, t R = 6.3 min (major) and t R = 7.2 min; RMS Calculated for C O 2 F 3 [M-] , found O O 2 3m (R)-3-(1-Furan-2-yl-2-nitroethyl)-1-indole: known compound 4 ; yellow oil; 98% yield; 88% ee; [α] 22 D = (c 1.64, C 2 Cl 2 ); [lit. 5 : [α] 20 D = (c 1.05, C 2 Cl 2 ) for 95% ee;]. R f = 0.33 (petroleum ether/etoac = 4/1); 1 MR (400 Mz, Acetone) δ (s, 1), 7.63 (d, S8
10 J = 8.0 z, 1), 7.48 (dd, J = 1.8, 0.7 z, 1), 7.44 (d, J = 8.1 z, 1), 7.36 (d, J = 2.5 z, 1), (m, 1), (m, 1), 6.36 (dd, J = 3.2, 1.9 z, 1), 6.29 (d, J = 3.2 z, 1), (m, 2), 5.15 (dd, J = 12.3, 7.3 z, 1); 13 C MR (101 Mz, Acetone) δ 154.2, 143.0, 137.7, , 124.1, 122.7, 120.1, 119.4, 112.5, 112.0, 111.2, 107.5, 78.6, 36.4; Daicel Chiralcel OD- column, hexane/i-pro = 70/30, Flow rate = 1.0 ml/min, UV = 254 nm, t R = 15.4 min (major) and t R = 21.8 min. 3n (R)-3-(1-(aphthalen-1-yl)-2-nitroethyl)-1-indole: known compound 4 : yellow oil; 95% yield; 95% ee; [α] 22 D = 22.5 (c 1.46, C 2 Cl 2 ); [lit. 5 : [α] 20 D = 25.8 (c 1.14, C 2 Cl 2 ) for 94% ee;] R f = 0.3 (petroleum ether/etoac = 4/1); 1 MR (400 Mz, CDCl 3 ) δ 8.29 (d, J = 8.3 z, 1), O (s, 1), (m, 1), 7.80 (m, 1), (m, 2), 7.46 (d, J = 8.0 z, 1), (m, 3), (m, 1), (m, 1), 7.00 (m, 1), 6.09 (t, J = 7.8 z, 1), (m, 2); 13 C MR (126 Mz, CDCl 3 ) δ 136.7, 134.8, 134.3, 131.3, 129.3, 128.5, 127.0, 126.3, 126.1, 125.5, 124.8, 122.8, 122.8, 120.1, 119.0, 114.5, 111.6, 78.7, 37.2; Daicel Chiralcel OD- column, hexane/i-pro = 70/30, Flow rate = 1.0 ml/min, UV = 254 nm, t R = 26.1 min (major) and t R = 31.5 min. 3o (R)-3-(2-aphthalen-1-yl-2-nitroethyl)-1-indole: known compond 7 ; white solid; m.p o C; 90% yield; 93% ee; [α] 26 D = (c 1.00, C 2 Cl 2 ); [lit. 7 : [α] 20 D = 18.9 (c 1.0, C 2 Cl 2 ) for 97% ee;] R f = 0.2 (petroleum ether/etoac = 4/1); 1 MR (400 Mz, Acetone) δ (s, O 1), 8.03 (s, 1), (m, 3), (m, 2), (m, 2 4), 7.13 (t, J = 7.6 z, 1), 7.00 (t, J = 7.5 z, 1), (m, 3); 13 C MR (101 Mz, Acetone) δ138.9, 137.8, 134.4, 133.6, 129.2, 128.6, 128.4, 127.3, , , , 123.1, 122.7, , 114.7, 112.4, 80.1, 42.5; Daicel Chiralpak AD-, hexane/i-pro = 90/10, Flow rate = 1.0 ml/min, UV = 210 nm, t R = 37.7 min and t R = 40.7 min (major). 3p (R)-3-(1-nitrohexan-2-yl)-1-indole: known compond 7 ; yellow oil; 65% yield; 70% ee; [α] 21 D = +9.7 (c 0.23, C 2 Cl 2 ); [lit. 7 : [α] D 20 = 30.6 O 2 (c 1.0, C 2 Cl 2 ) for 91% ee;] R f = 0.33 (petroleum ether/etoac = 8/1); 1 MR (400 Mz, Acetone) δ (s, 1), 7.67 (d, J = 7.9 z, 1), 7.41 (d, J = 8.1 z, 1), 7.28 (s, 1), 7.12 (t, J = 7.5 z, 1), 7.04 (t, J = 7.5 z, 1), 4.83 (d, J = 7.6 z, 2), 3.80 (m, 1), (m, 2), (m, 4), 0.83 (t, J = 6.5 z, 3);. 13 C MR (101 Mz, Acetone) δ 137.8, 127.5, 123.5, 122.4, 119.8, 119.4, 114.5, 112.5, 81.3, 37.0, 33.2, 30.1, 23.2, 14.2; PLC: Daicel Chiralcel OD- column, hexane/i-pro = 90/10, Flow rate = 1.0 ml/min, UV = 254 nm, t R = 35.7 min (major) and t R = 39.3 min. O 2 3q (R)-5-Methyl-3-(2-nitro-1-phenylethyl)-1-indole: known compond 8 ; white solid; m.p o C; 99% yield; 94% ee; [α] 26 D = (c 1.38, C 2 Cl 2 ); [lit. 8 : [α] 20 D = +9.7 (c 0.92, C 2 Cl 2 ) for 97% ee;] R f = 0.27 (petroleum ether/etoac = 4/1); 1 MR (400 Mz, Acetone) δ 7 Ganesh, M.; Seidel, D. J. Am. Chem. Soc. 2008, 130, Liu,.; Du, D.-M. Adv. Synth. Catal. 2010, 352, S9
11 10.11 (s, 1), (m, 2), (m, 5), (m, 1), 6.97 (dd, J = 8.3, 1.4 z, 1), (m, 3), 2.37 (s, 3); 13 C MR (101 Mz, Acetone) δ 141.5, 136.1, 129.4, 128.8, 127.9, 127.6, 124.3, 123.0, 119.0, 114.3, 112.1, 80.2, 42.3, 21.6; PLC: Daicel Chiralpak AD-, hexane/i-pro = 80/20, Flow rate = 1.0 ml/min, UV = 254 nm, t R = 25.9 min (major) and t R = 30.9 min. MeO O 2 3r (R)-5-Methoxy-3-(2-nitro-1-phenylethyl)-1-indole: known compound 5 ; white solid; m.p o C; 99% yield; 95% ee; [α] 20 D = (c 1.96, C 2 Cl 2 ); [lit. 5 : [α] 20 D = (c 1.02, C 2 Cl 2 ) for 96% ee;] R f = 0.21 (petroleum ether/etoac = 4/1); 1 MR (500 Mz, CDCl 3 ) δ 7.99 (s, 1), (m, 4), (m, 2), 7.00 (d, J = 2.3 z, 1), 6.84 (dt, J = 5.8, 2.4 z, 2), 5.14 (t, J = 8.0 z, 1), 5.04 (dd, J = 12.5, 7.6 z, 1), 4.93 (dd, J = 12.5, 8.4 z, 1), 3.77 (s, 3); 13 C MR (126 Mz, CDCl 3 ) δ 154.3, 139.3, 131.7, 129.1, 127.9, 127.7, 126.7, 122.4, 114.2, 112.9, 112.2, 100.9, 79.6, 56.0, Daicel Chiralpak AD-, hexane/i-pro = 90/10, Flow rate = 1.0 ml/min, UV = 210 nm, t R = 28.0 min (major) and t R = 42.5 min. F O 2 3s (R)-5-Fluoro-3-(2-nitro-1-phenylethyl)-1-indole: known compond 9 ; yellow oil; 88% yield; 94% ee; [α] 20 D = (c 1.79, C 2 Cl 2 ); R f = 0.25 (petroleum ether/etoac = 8/1); 1 MR (400 Mz, Acetone) δ (s, 1), (m, 3), 7.41 (dd, J = 8.8, 4.5 z, 1), 7.33 (m, 2), 7.23 (ddd, m, 2), 6.92 (td, J = 9.1, 2.5 z, 1), (m, 3); 13 C MR (101 Mz, Acetone) δ (d, J C-F = z), 141.2, 134.3, 129.5, 128.8, 128.0, (d, J C-F = 9.8 z), 125.0, (d, J C-F = 4.8 z), (d, J C-F = 9.8 z), (d, J C-F = 26.4 z), (d, J C-F = 23.8 z), 80.0, 42.1; Daicel Chiralpak AD-, hexane/i-pro = 90/10, Flow rate = 1.0 ml/min, UV = 210 nm, t R = 19.1 min (major) and t R = 22.7 min. Br O 2 3t (R)-5-Bromo-3-(2-nitro-1-phenylethyl)-1-indole: known compound 5 ; yellow oil; 99% yield; 94% ee; [α] 26 D = (c 1.58, C 2 Cl 2 ); [lit. 5 : [α] 20 D = (c 1.11, C 2 Cl 2 ) for 93% ee;] R f = 0.17 (petroleum ether/etoac = 8/1); 1 MR (400 Mz, CDCl 3 ) δ 8.12 (s, 1), 7.54 (d, J = 1.6 z, 1), (m, 7), 7.04 (d, J = 2.4 z, 1), 5.11 (t, J = 8.0 z, 1), 5.01 (dd, J = 12.5, 8.0 z, 1), 4.90 (dd, J = 12.5, 8.0 z, 1); 13 C MR (101 Mz, CDCl 3 ) δ 138.8, 135.2, 129.2, 128.0, 127.9, 127.8, 125.8, 122.9, 121.6, 114.2, 113.4, 113.0, 79.5, 41.4; Daicel Chiralpak AD-, hexane/i-pro = 90/10, Flow rate = 1.0 ml/min, UV = 254 nm, t R = 18.0 min (major) and t R = 19.6 min. 9 Singh, P. K.; Bisai, A.; Singh, V. K. Tetrahedron Lett. 2007, 48, S10
12 Copy of MR Ts L1 Ts Ts Ts L1 S11
13 Ts L2 Ts Ts L2 Ts S12
14 Ts L3 Ts Ts L3 Ts S13
15 Ts L4 Ts Ts L4 Ts S14
16 Bn Ts Ts L5 Bn Bn Ts Ts L5 Bn S15
17 Ts Ts L6 Ts Ts L6 S16
18 Ts L7 Ts Ts L7 Ts S17
19 O 2 3a O 2 3a S18
20 Cl O 2 3b Cl O 2 3b S19
21 Cl O 2 3c Cl O 2 3c S20
22 Cl O 2 3d Cl O 2 3d S21
23 O 2 3e O 2 3e S22
24 MeO O 2 3f MeO O 2 3f S23
25 OMe O 2 3g OMe O 2 3g S24
26 Br O 2 3h Br O 2 3h S25
27 Br O 2 3i Br O 2 3i S26
28 Br O 2 3j Br O 2 3j S27
29 F O 2 3k F O 2 3k S28
30 CF 3 O 2 3l CF 3 O 2 3l S29
31 O O 2 3m O O 2 3m S30
32 O 2 3n O 2 3n S31
33 O 2 3o O 2 3o S32
34 O 2 3p O 2 3p S33
35 O 2 3q O 2 3q S34
36 MeO O 2 3r MeO O 2 3r S35
37 F O 2 3s F O 2 3s S36
38 Br O 2 3t Br O 2 3t S37
39 Copy of PLC for racemic and chiral compounds O 2 (+/-) 3aa O 2 3aa 95% ee S38
40 Cl Cl O 2 O 2 (+/-) 3ab 3ab 92% ee S39
41 Cl Cl O 2 O 2 (+/-) 3ac 3ac 94% ee S40
42 Cl Cl O 2 O 2 (+/-) 3ad 3ad 97% ee S41
43 O 2 O 2 (+/-) 3ae 3ae 93% ee S42
44 MeO MeO O 2 (+/-) 3af O 2 3af 88% ee S43
45 OMe OMe (+/-) 3ag O 2 3ag 93% ee O 2 S44
46 Br Br O 2 O 2 (+/-) 3ah 3ah 96% ee S45
47 Br Br O 2 O 2 (+/-) 3ai 3ai 93% ee S46
48 Br Br O 2 O 2 (+/-) 3aj 3aj 92% ee S47
49 F F O 2 O 2 (+/-) 3ak 3ak 96% ee S48
50 CF 3 CF 3 O 2 O 2 (+/-) 3al 3al 94% ee S49
51 O O 2 O O 2 (+/-) 3am 3am 88% ee S50
52 O 2 O 2 (+/-) 3an 3an 95% ee S51
53 O 2 O 2 (+/-) 3ao 3ao 93% ee S52
54 O 2 O 2 (+/-) 3ap 3ap 70% ee S53
55 O 2 O 2 (+/-) 3ba 3ba 94% ee S54
56 MeO O 2 MeO (+/-) 3ca O 2 3ca 95% ee S55
57 F O 2 F O 2 (+/-) 3da 3da 94% ee S56
58 Br O 2 Br O 2 (+/-) 3ea 3ea 94% ee S57
59 Ts Ts S58
60 Ts Ts S59
61 Ts Ts S60
62 Bn Ts Ts Bn S61
63 Ts Ts S62
64 Ts Ts S63
65 F O 2 S64
66 CF 3 O 2 S65
Supporting Information
Supporting Information Lewis acid catalyzed ring-opening reactions of methylenecyclopropanes with diphenylphosphine oxide in the presence of sulfur or selenium Min Shi,* Min Jiang and Le-Ping Liu State
Supporting Information. Asymmetric Binary-acid Catalysis with Chiral. Phosphoric Acid and MgF 2 : Catalytic
Supporting Information Asymmetric Binary-acid Catalysis with Chiral Phosphoric Acid and MgF 2 : Catalytic Enantioselective Friedel-Crafts Reactions of β,γ- Unsaturated-α-Ketoesters Jian Lv, Xin Li, Long
A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes
Copper-Catalyzed Oxidative Dehydrogenative N-N Bond. Formation for the Synthesis of N,N -Diarylindazol-3-ones
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2016 Supporting information Copper-Catalyzed Oxidative Dehydrogenative - Bond Formation
Mandelamide-Zinc Catalyzed Alkyne Addition to Heteroaromatic Aldehydes
1 Mandelamide-Zinc Catalyzed Alkyne Addition to Heteroaromatic Aldehydes Gonzalo Blay, Isabel Fernández, Alícia Marco-Aleixandre, and José R. Pedro Departament de Química Orgànica, Facultat de Química,
Supporting Information One-Pot Approach to Chiral Chromenes via Enantioselective Organocatalytic Domino Oxa-Michael-Aldol Reaction
Supporting Information ne-pot Approach to Chiral Chromenes via Enantioselective rganocatalytic Domino xa-michael-aldol Reaction Hao Li, Jian Wang, Timiyin E-Nunu, Liansuo Zu, Wei Jiang, Shaohua Wei, *
Supporting Information
Supporting Information for Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction Chun-Huan Jiang, Xiantao Lei,
Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic acids with the assistance of isocyanide
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic
Supporting Information
Supporting Information Montmorillonite KSF-Catalyzed One-pot, Three-component, Aza-Diels- Alder Reactions of Methylenecyclopropanes With Arylaldehydes and Aromatic Amines Li-Xiong Shao and Min Shi* General
Supporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Synthesis of 3-omosubstituted Pyrroles via Palladium- Catalyzed Intermolecular Oxidative Cyclization
Direct Palladium-Catalyzed Arylations of Aryl Bromides. with 2/9-Substituted Pyrimido[5,4-b]indolizines
![Direct Palladium-Catalyzed Arylations of Aryl Bromides. with 2/9-Substituted Pyrimido[5,4-b]indolizines](/thumbs/87/95187440.jpg "Direct Palladium-Catalyzed Arylations of Aryl Bromides. with 2/9-Substituted Pyrimido[5,4-b]indolizines")
Direct Palladium-Catalyzed Arylations of Aryl Bromides with 2/9-Substituted Pyrimido[5,4-b]indolizines Min Jiang, Ting Li, Linghua Meng, Chunhao Yang,* Yuyuan Xie*, and Jian Ding State Key Laboratory of
Metal-free Oxidative Coupling of Amines with Sodium Sulfinates: A Mild Access to Sulfonamides
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting information for Metal-free Oxidative Coupling of Amines with Sodium Sulfinates:
Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process
Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process Jincan Zhao 1, Hong Fang 1, Jianlin Han* 1,2 and Yi Pan* 1
Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%.
Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%. S1 Supplementary Figure S2. Single X-ray structure 5a at probability ellipsoids of 20%. S2 H 15 Ph Ac Ac I AcH Ph Ac
Supporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2010 A Highly Effective Bis(sulfonamide) Diamine Ligand: A Unique Chiral Skeleton for the Enantioselective Cu-Catalyzed
ESI for. A simple and efficient protocol for the palladium-catalyzed. ligand-free Suzuki reaction at room temperature in aqueous DMF.
ESI for A simple and efficient protocol for the palladium-catalyzed ligand-free Suzuki reaction at room temperature in aqueous DMF Chun Liu,* Qijian i, Fanying Bao and Jieshan Qiu State Key Laboratory
Supporting Information
Supporting Information Copper/Silver Cocatalyzed Oxidative Coupling of Vinylarenes with ICH 2 CF 3 or ICH 2 CHF 2 Leading to β-cf 3 /CHF 2 -Substituted Ketones Niannian Yi, Hao Zhang, Chonghui Xu, Wei
and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol
FeCl 3 6H 2 O-Catalyzed Disproportionation of Allylic Alcohols and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol Jialiang Wang, Wen Huang, Zhengxing Zhang, Xu
Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent
Supplementary information for the paper Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent Yang Xue, Ling-Po Li, Yan-Hong He * & Zhi Guan * School of Chemistry and Chemical Engineering,
Rh(III)-Catalyzed C-H Amidation with N-hydroxycarbamates: A. new Entry to N-Carbamate Protected Arylamines
Rh(III)-Catalyzed C-H Amidation with N-hydroxycarbamates: A new Entry to N-Carbamate Protected Arylamines Bing Zhou,* Juanjuan Du, Yaxi Yang,* Huijin Feng, Yuanchao Li Shanghai Institute of Materia Medica,
Supporting information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting information Copper-catalysed intramolecular O-arylation: a simple
Supporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information Silver or Cerium-Promoted Free Radical Cascade Difunctionalization
The N,S-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H. Carbonylation using Langlois Reagent as CO Source. Supporting Information.
Electronic upplementary Material (EI) for rganic & Biomolecular Chemistry. This journal is The Royal ociety of Chemistry 2018 The,-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H Carbonylation using
Chiral Brønsted Acid Catalyzed Enantioselective Intermolecular Allylic Aminations. Minyang Zhuang and Haifeng Du*
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Chiral Brønsted Acid Catalyzed Enantioselective Intermolecular Allylic
Highly enantioselective cascade synthesis of spiropyrazolones. Supporting Information. NMR spectra and HPLC traces
Highly enantioselective cascade synthesis of spiropyrazolones Alex Zea a, Andrea-Nekane R. Alba a, Andrea Mazzanti b, Albert Moyano a and Ramon Rios a,c * Supporting Information NMR spectra and HPLC traces
Supplementary Figure 1. (X-ray structures of 6p and 7f) O N. Br 6p
Supplementary Figure 1 (X-ray structures of 6p and 7f) Me Br 6p 6p Supplementary Figures 2-68 (MR Spectra) Supplementary Figure 2. 1 H MR of the 6a Supplementary Figure 3. 13 C MR of the 6a Supplementary
Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3
Supporting Information Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3 Shohei Shimokawa, Yuhsuke Kawagoe, Katsuhiko Moriyama, Hideo Togo* Graduate
SUPPLEMENTARY INFORMATION
SUPPLEMETARY IFRMATI DI: 10.1038/CEM.1406 ighly enantioselective trapping of zwitterionic intermediates by imines uang Qiu,a, Ming Li,a, Li-Qin Jiang a, Feng-Ping Lv a, Li Zan a, Chang-Wei Zhai a, Michael.
Aminofluorination of Fluorinated Alkenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Synthesis of ɑ CF 3 and ɑ CF 2 H Amines via Aminofluorination of Fluorinated Alkenes Ling Yang,
Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes
Supporting Information for Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes Changkun Li and Jianbo Wang* Beijing National Laboratory
Construction of Cyclic Sulfamidates Bearing Two gem-diaryl Stereocenters through a Rhodium-Catalyzed Stepwise Asymmetric Arylation Protocol
Supporting Information for: Construction of Cyclic Sulfamidates Bearing Two gem-diaryl Stereocenters through a Rhodium-Catalyzed Stepwise Asymmetric Arylation Protocol Yu-Fang Zhang, Diao Chen, Wen-Wen
Supporting Information
Supporting Information Ceric Ammonium Nitrate (CAN) catalyzed efficient one-pot three component aza-diels-alder reactions for a facile synthesis of tetrahydropyranoquinoline derivatives Ravinder Goud Puligoundla
Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles
Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry SUPPRTIG IFRMATI Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles Anahit Pews-Davtyan and Matthias Beller* Leibniz-Institut
Synthesis of Imines from Amines in Aliphatic Alcohols on Pd/ZrO 2 Catalyst at Ambient Conditions
This journal is The Royal Society of Chemistry 213 Synthesis of Imines from Amines in Aliphatic Alcohols on Pd/ZrO 2 Catalyst at Ambient Conditions Wenjing Cui, a Bao Zhaorigetu,* a Meilin Jia, a and Wulan
Electronic Supplementary Information
Electronic Supplementary Information Unprecedented Carbon-Carbon Bond Cleavage in Nucleophilic Aziridine Ring Opening Reaction, Efficient Ring Transformation of Aziridines to Imidazolidin-4-ones Jin-Yuan
Hiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl
Hiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl Philippe Pierrat, Philippe Gros* and Yves Fort Synthèse Organométallique
Iodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via double C(sp 2 )-H thiolation
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Iodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via
Supporting Information
Supporting Information for AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds Qiuping Ding 1, Dan Wang 1, Puying Luo* 2, Meiling Liu 1, Shouzhi Pu* 3 and
Ligand-free Cu(II)-mediated aerobic oxidations of aldehyde. hydrazones leading to N,N -diacylhydrazines and 1,3,4-oxadiazoles
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Ligand-free Cu(II)-mediated aerobic oxidations of aldehyde hydrazones leading
Vilsmeier Haack reagent-promoted formyloxylation of α-chloro-narylacetamides
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 205 Vilsmeier aack reagent-promoted formyloxylation of α-chloro-arylacetamides by formamide Jiann-Jyh
Electronic Supplementary Information
Electronic Supplementary Information NbCl 3 -catalyzed [2+2+2] intermolecular cycloaddition of alkynes and alkenes to 1,3-cyclohexadiene derivatives Yasushi Obora,* Keisuke Takeshita and Yasutaka Ishii*
Supplementary Information for
Supplementary Information for Organocatalytic Asymmetric Intramolecular [3+2] Cycloaddition: A Straightforward Approach to Access Multiply Substituted Hexahydrochromeno[4,3-b]pyrrolidine Derivatives in
Supporting Information for
Supporting Information for Palladium-Catalyzed C-H Bond Functionalization of C6-Arylpurines Hai-Ming Guo,* Wei-Hao Rao, Hong-Ying iu, Li-Li Jiang, Ge ng, Jia-Jia Jin, Xi-ing Yang, and Gui-Rong Qu* College
Supporting Information. Table of Contents. II. Experimental procedures. II. Copies of 1H and 13C NMR spectra for all compounds
Electronic upplementary Material (EI) for rganic & Biomolecular Chemistry. This journal is The Royal ociety of Chemistry 2017 Laboratoire de Méthodologie et ynthèse de Produit aturels. Université du Québec
Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate
upporting Information Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate Jing-Yu Wu, Zhi-Bin Luo, Li-Xin Dai and Xue-Long Hou* a tate Key Laboratory of Organometallic
Supporting Information for
Supporting Information for An atom-economic route to densely functionalized thiophenes via base-catalyzed rearrangement of 5-propargyl-2H-thiopyran-4(3H)-ones Chunlin Tang a, Jian Qin b, Xingqi Li *a a
Supporting Information
Supporting Information Wiley-VC 007 9 Weinheim, Germany ew ear Infrared Dyes and Fluorophores Based on Diketopyrrolopyrroles Dipl.-Chem. Georg M. Fischer, Dipl.-Chem. Andreas P. Ehlers, Prof. Dr. Andreas
Free Radical Initiated Coupling Reaction of Alcohols and. Alkynes: not C-O but C-C Bond Formation. Context. General information 2. Typical procedure 2
Free Radical Initiated Coupling Reaction of Alcohols and Alkynes: not C-O but C-C Bond Formation Zhongquan Liu,* Liang Sun, Jianguo Wang, Jie Han, Yankai Zhao, Bo Zhou Institute of Organic Chemistry, Gannan
Supporting Information
Supporting Information Wiley-VCH 2014 69451 Weinheim, Germany Copper-Catalyzed Coupling of Oxime Acetates with Sodium Sulfinates: An Efficient Synthesis of Sulfone Derivatives** Xiaodong Tang, Liangbin
Fluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine Reagents. An Efficient Method for 1,3- Oxyfluorination and 1,3-Difluorination
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2016 Supporting Information Fluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine
Divergent synthesis of various iminocyclitols from D-ribose
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 205 Divergent synthesis of various iminocyclitols from D-ribose Ramu Petakamsetty,
Supporting Information. Consecutive hydrazino-ugi-azide reactions: synthesis of acylhydrazines bearing 1,5- disubstituted tetrazoles
Supporting Information for Consecutive hydrazino-ugi-azide reactions: synthesis of acylhydrazines bearing 1,5- disubstituted tetrazoles Angélica de Fátima S. Barreto*, Veronica Alves dos Santos, and Carlos
Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst- and solvent-free thermal multicomponent domino reaction
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 SUPPRTIG IFRMATI Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst-
Supporting Information. Experimental section
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Experimental section General. Proton nuclear magnetic resonance ( 1
Copper-Catalyzed Direct Acyloxylation of C(sp 2 ) H Bonds. in Aromatic Amides
Supporting Information for Copper-Catalyzed Direct Acyloxylation of C(sp 2 ) H Bonds in Aromatic Amides Feifan Wang, Qiyan Hu, Chao Shu, Zhiyang Lin, Dewen Min, Tianchao Shi and Wu Zhang* Key Laboratory
Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 1 A Facile Way to Synthesize 2H-Chromenes: Reconsideration of the Reaction Mechanism between Salicylic Aldehyde and
The Free Internet Journal for Organic Chemistry
The Free Internet Journal for Organic Chemistry Paper Archive for Organic Chemistry Arkivoc 2018, part iii, S1-S6 Synthesis of dihydropyranones and dihydropyrano[2,3- d][1,3]dioxine-diones by cyclization
Room Temperature Highly Diastereoselective Zn-Mediated. Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled
Supporting Information for: Room Temperature Highly Diastereoselective Zn-Mediated Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled Stereoselectivity Reversal
Electronic Supplementary Information (ESI)
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Electronic Supplementary Information (ESI) For Iron-Catalysed xidative Amidation of Alcohols with Amines Silvia Gaspa, a Andrea
Supporting Information For: Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes
Supporting Information For: Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes Xiao-Hui Yang and Vy M. Dong* dongv@uci.edu Department of Chemistry, University
Copper-Catalyzed Oxidative Coupling of Acids with Alkanes Involving Dehydrogenation: Facile Access to Allylic Esters and Alkylalkenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supplementary information Copper-Catalyzed xidative Coupling of Acids with Alkanes Involving Dehydrogenation:
gem-dichloroalkenes for the Construction of 3-Arylchromones
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Pd(OAc)2/S=PPh3 Accelerated Activation of gem-dichloroalkenes for the Construction of 3-Arylchromones
Synthesis of unsymmetrical imidazolium salts by direct quaternization of N-substituted imidazoles using arylboronic acids
Electronic Supplementary Material (ESI) for Chemical Communications. This journal is The Royal Society of Chemistry 2014 Supporting Information Synthesis of unsymmetrical imidazolium salts by direct quaternization
Supporting Information Table of Contents 1. General remarks...s1 2. Synthesis of catalyst L S1
Diastereo- and Enantioselective Conjugate Addition of 3-Substituted xindoles to itroolefins Catalyzed by a Chiral i(ac) 2 -Diamine Complex under Mild Conditions Yan-Yan Han,, Zhi-Jun Wu, Wen-Bing Chen,,
Site-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran
1 Site-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran Munawar Hussain, a Rasheed Ahmad Khera, a Nguyen Thai Hung, a Peter Langer* a,b a Institut für Chemie, Universität Rostock,
Supporting Information for
Supporting Information for A ovel Synthesis of luorinated Pyrazoles via Gold(I)-Catalyzed Tandem Aminofluorination of Alkynes in the Presence of Selectfluor Jianqiang Qian, Yunkui Liu,* Jie Zhu, Bo Jiang,
Supplementary Information. Bio-catalytic asymmetric Mannich reaction of ketimines using. wheat germ lipase
Electronic Supplementary Material (ESI) for Catalysis Science & Technology. This journal is The Royal Society of Chemistry 2016 Supplementary Information Bio-catalytic asymmetric Mannich reaction of ketimines
Supporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information 1. General experimental methods (S2). 2. Table 1: Initial studies (S2-S4).
Transfer of axial chirality through the nickel-catalyzed hydrocyanation of chiral allenes
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 7 Electronic supplementary information for Transfer of axial chirality through
Supporting Information for Synthesis of Fused N-Heterocycles via Tandem C-H Activation
This journal is The Royal Society of Chemistry 212 Supporting Information for Synthesis of Fused -Heterocycles via Tandem C-H Activation Ge Meng, Hong-Ying iu, Gui-Rong Qu, John S. Fossey, Jian-Ping Li,*
Supplementary information
Electronic Supplementary Material (ESI) for MedChemComm. This journal is The Royal Society of Chemistry 2015 Supplementary information Synthesis of carboxyimidamide-substituted benzo[c][1,2,5]oxadiazoles
Synthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and D-homoandrostane. Tandem Click reaction/cu-catalyzed D-homo rearrangement
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information Synthesis of novel 1,2,3-triazolyl derivatives of
SUPPORTING INFORMATION
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 SUPPORTIG IFORMATIO Visible light-mediated decarboxylative amination of indoline-2- carboxylic
Supporting Information
Electronic Supplementary Material (ESI) for rganic Chemistry Frontiers. This journal is the Partner rganisations 2018 Palladium-catalyzed direct approach to α-cf 3 aryl ketones from arylboronic acids Bo
Rhodium-Catalyzed Oxidative Decarbonylative Heck-type Coupling of Aromatic Aldehydes with Terminal Alkenes
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information Rhodium-Catalyzed Oxidative Decarbonylative Heck-type
Chiral Phosphoric acid Catalyzed Enantioselective N- Alkylation of Indoles with in situ Generated Cyclic N-Acyl Ketimines
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Chiral osphoric acid Catalyzed Enantioselective - Alkylation of Indoles with in situ Generated
9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer catalysts
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer
Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes
![Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes](/thumbs/61/45469742.jpg "Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes")
Supporting Information for Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes Yibiao Li* 1, Liang Cheng 1, Xiaohang Liu
SUPPORTING INFORMATION. Transition Metal-Free Arylations of In-Situ Generated Sulfenates with Diaryliodonium Salts
S1 SUPPORTING INFORMATION Transition Metal-Free Arylations of In-Situ Generated Sulfenates with Diaryliodonium Salts Hao Yu, Zhen Li, and Carsten Bolm* Institute of Organic Chemistry, RWTH Aachen University
Cu(I)-Catalyzed Asymmetric Multicomponent Cascade Inverse. Electron-Demand aza-diels-alder/nucleophilic Addition/Ring-Opening
Cu(I)-Catalyzed Asymmetric Multicomponent Cascade Inverse Electron-Demand aza-diels-alder/nucleophilic Addition/Ring-Opening Reaction Involving 2-Methoxyfurans as Efficient Dienophiles Rong Huang, Xin
Supporting Information for. Copper-Catalyzed Radical Reaction of N-Tosylhydrazones: Stereoselective Synthesis of (E)-Vinyl Sulfones
Supporting Information for Copper-Catalyzed Radical Reaction of N-Tosylhydrazones: Stereoselective Synthesis of (E)-Vinyl Sulfones Shuai Mao, Ya-Ru Gao, Xue-Qing Zhu, Dong-Dong Guo, Yong-Qiang Wang* Key
Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone.
Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone. Won-Suk Kim, Hyung-Jin Kim and Cheon-Gyu Cho Department of Chemistry, Hanyang University, Seoul 133-791, Korea Experimental Section
Phosphorus Oxychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions
Supplementary Information for Phosphorus xychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions u Chen,* a,b Xunfu Xu, a Liu Liu, a Guo Tang,* a
Heterobimetallic Pd-Sn Catalysis: Michael Addition. Reaction with C-, N-, O-, S- Nucleophiles and In-situ. Diagnostics
Supporting Information (SI) Heterobimetallic Pd-Sn Catalysis: Michael Addition Reaction with C-, N-, -, S- Nucleophiles and In-situ Diagnostics Debjit Das, a Sanjay Pratihar a,b and Sujit Roy c * a rganometallics
Supplementary Material
Supplementary Material Chiral N-aryl tert-butanesulfinamide-olefin ligands for rhodium-catalyzed asymmetric 1,4-addition Shuai Yuan, Qingle Zeng,* Jiajun Wang, Lihong Zhou State Key Laboratory of Geohazard
Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information
![Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information](/thumbs/64/50937700.jpg "Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information")
Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans Liang Yun, Shi Tang, Xu-Dong Zhang, Li-Qiu Mao, Ye-Xiang Xie and Jin-Heng Li* Key Laboratory
Sequential catalysis for the production of sterically hindered amines: Ruthenium(II)-catalyzed C-H bond activation and hydrosilylation of imines
Electronic Supporting Information Sequential catalysis for the production of sterically hindered amines: Ruthenium(II)-catalyzed C- bond activation and hydrosilylation of imines Bin Li, Charles B. Bheeter,
Supporting information
Electronic upplementary Material (EI) for New Journal of Chemistry. This journal is The Royal ociety of Chemistry and the Centre National de la Recherche cientifique 7 upporting information Lipase catalyzed,-addition
First DMAP-mediated direct conversion of Morita Baylis. Hillman alcohols into γ-ketoallylphosphonates: Synthesis of
Supporting Information File 1 for First DMAP-mediated direct conversion of Morita Baylis Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates Marwa Ayadi 1,2, Haitham Elleuch
Supporting Information
Supporting Information 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Convenient and General Zinc-Catalyzed Borylation of Aryl Diazonium Salts and Aryltriazenes under Mild Conditions
Sotto, 8; Perugia, Italia. Fax: ; Tel: ;
ELECTRONIC SUPPORTING INFORMATION Ermal Ismalaj a, Giacomo Strappaveccia a, Eleonora Ballerini a, Fausto Elisei a, Oriana Piermatti a, Dmitri Gelman b, Luigi Vaccaro a a CEMIN - Dipartimento di Chi mica,
Zuxiao Zhang, Xiaojun Tang and William R. Dolbier, Jr.* Department of Chemistry, University of Florida, Gainesville, FL
Photoredox-Catalyzed Intramolecular Difluoromethylation of -Benzylacrylamides Coupled with a Dearomatizing Spirocyclization: Access to CF2H Containing 2- Azaspiro[4.5]deca-6,9-diene-3,8-diones. Zuxiao
Supporting Information
Electronic upplementary Material (EI) for Green Chemistry. This journal is The Royal ociety of Chemistry 204 upporting Information ynthesis of sulfonamides via I 2 -mediated reaction of sodium sulfinates
Supporting Information for. Rhodium-Catalyzed β-selective Oxidative Heck-Type
Supporting Information for Rhodium-Catalyzed β-selective Oxidative Heck-Type Coupling of Vinyl Acetate via C-H Activation Hui-Jun Zhang,* Weidong Lin, Feng Su, and Ting-Bin Wen* Department of Chemistry,
Facile construction of the functionalized 4H-chromene via tandem. benzylation and cyclization. Jinmin Fan and Zhiyong Wang*
Facile construction of the functionalized 4H-chromene via tandem benzylation and cyclization Jinmin Fan and Zhiyong Wang* Hefei National Laboratory for Physical Science at Microscale, Joint- Lab of Green
D-Glucosamine-derived copper catalyst for Ullmann-type C- N coupling reaction: theoretical and experimental study
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 D-Glucosamine-derived copper catalyst for Ullmann-type C- N coupling reaction: theoretical
Supporting Information
Supporting Information Rhodium-catalyzed Intramolecular Dehydrogenative Aryl Aryl Coupling Using Air as Terminal Oxidant Hannah Baars, 1,2 Yuto Unoh, 1 Takeshi Okada, 1 Koji Hirano, 1 Tetsuya Satoh,* 1,3
Supporting Information for
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information for Quinine-Catalyzed Highly Enantioselective Cycloannulation
Cu-Catalyzed/Mediated Synthesis of N-Fluoroalkylanilines from Arylboronic Acids: Fluorine Effect on the Reactivity of Fluoroalkylamines
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 S1 Cu-Catalyzed/Mediated Synthesis of N-Fluoroalkylanilines from Arylboronic
Supporting Information
Supporting Information An Approach to 3,6-Disubstituted 2,5-Dioxybenzoquinones via Two Sequential Suzuki Couplings. Three-step Synthesis of Leucomelone Xianwen Gan, Wei Jiang, Wei Wang,,,* Lihong Hu,,*