Supporting Information
|
|
- Ανυβις Βικελίδης
- 5 χρόνια πριν
- Προβολές:
Transcript
1 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 Deng*, Ruijia Wang, Dongming Peng, Zebing Zeng, and Jiannan Xiang* State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, , P. R. China School of Pharmacy, Hunan University of Chinese Medicine, Changsha, , P. R. China Content Page number General information 1 General procedure 1 Mechanistic study 1 Characterization data of products 2 1 H, 13 C and 19 F NMR spectra 10
2 General information Commercially available reagents were purchased from commercial suppliers and used without further purification. Reactions were monitored by thin layer chromatography (TLC) using silicycle pre-coated silica gel plates. Flash column chromatography was performed over silicycle silica gel ( mesh). 1 H NMR, 13 C NMR and 19 F NMR spectra were recorded on 400 MHz NMR plus spectrometer using residue solvent peaks as internal standards. Infrared spectra were recorded with IR spectrometer and are reported in reciprocal centimeter (cm -1 ). High resolution mass spectra were obtained using GCT-TOF instrument with EI or ESI source. General procedure for the synthesis of 3 and 4 To a sealed tube were added vinylarene (0.75 mmol), ICH 2 CF 3 (0.5 mmol, 105 mg) or ICH 2 CHF 2 (0.5 mmol, 96 mg), Cu(acac) 2 (0.1 mmol, 26 mg), Ag 2 SO 4 (0.1 mmol, 31 mg), Et 3 N (0.5 mmol, 50 mg), TBHP (1.5 mmol, 193 mg, 70% in water) and CH 3 CN (1 ml). Then the tube was stirred at 80 C for 24 h. After completion of the reaction, the resulting mixture was diluted with dichloromethane and washed with water. The separated aqueous phase was washed with CH 2 Cl 2. The combined organic layers were washed with brine, dried over Na 2 SO 4, filtered, and concentrated under vacuo. The crude mixture was purified by column chromatography on silica gel (petroleum ether/ethyl acetate) to afford the desired product 3 or 4. Large-scale synthesis of 3a To a sealed tube were added 4-tert-butylstyrene (15 mmol, 2.4 g), ICH 2 CF 3 (10 mmol, 2.1 g), Cu(acac) 2 (2 mmol, 0.52 g), Ag 2 SO 4 (2 mmol, 0.62 g), Et 3 N (10 mmol, 1.0 g), TBHP (30 mmol, 3.86 g, 70% in water) and CH 3 CN (20 ml). Then the tube was stirred at 80 C for 24 h. After completion of the reaction, the resulting mixture was quenched with saturated Na 2 S 2 O 3 solution and extracted with dichloromethane. The organic layer was washed with water and brine, and the separated aqueous phase was extracted with CH 2 Cl 2. The combined organic layers dried over Na 2 SO 4, filtered, and concentrated under vacuo. The crude mixture was purified by column chromatography on silica gel (petroleum ether/ethyl acetate) to afford the desired product 3a as a white solid (1.56 g, 60% yield). Mechanistic study 1) The reaction of TEMPO and ICH 2 CF 3 under the standard conditions To a sealed tube were added ICH 2 CF 3 (0.5 mmol, 105 mg), TEMPO (1.0 mmol, 156 mg), Cu(acac) 2 (0.1 mmol, 26 mg), Ag 2 SO 4 (0.1 mmol, 31 mg), Et 3 N (0.5 mmol, 50 mg), TBHP (1.5 mmol, 193 mg, 70% in water) and CH 3 CN (2 ml). Then the tube was stirred at 80 C for 24 h. After completion of the reaction, the resulting mixture was diluted with dichloromethane and washed with water. The separated aqueous phase was washed with CH 2 Cl 2. The combined organic layers were dried over Na 2 SO 4, filtered, and concentrated under vacuo. 19 F NMR analysis of the 1
3 crude mixture showed that TEMPO-CH 2 CF 3 was formed in 71% yield. EI-MS (m/z, relative intensity): 239 (M +, 11), 224 (100), 156 (71), 124 (27), 109 (68), 69 (80). 19 F NMR (376 MHz, CDCl 3 ) δ ) The reaction of 4-tert-butylstyrene, TEMPO and ICH 2 CF 3 under the standard conditions To a sealed tube were added 4-tert-butylstyrene (0.75 mmol, 120 mg), ICH 2 CF 3 (0.5 mmol, 105 mg), TEMPO (1.0 mmol, 156 mg), Cu(acac) 2 (0.1 mmol, 26 mg), Ag 2 SO 4 (0.1 mmol, 31 mg), Et 3 N (0.5 mmol, 50 mg), TBHP (1.5 mmol, 193 mg, 70% in water) and CH 3 CN (2 ml). Then the tube was stirred at 80 C for 24 h. After completion of the reaction, the resulting mixture was diluted with dichloromethane and washed with water. The separated aqueous phase was washed with CH 2 Cl 2. The combined organic layers were dried over Na 2 SO 4, filtered, and concentrated under vacuo. 19 F NMR analysis of the crude mixture showed that TEMPO-CH 2 CF 3 was formed in 60% yield and 3a was not detected. Characterization data of products 1-(4-(tert-butyl)phenyl)-4,4,4-trifluorobutan-1-one (3a) White solid, 62% yield (80 mg), mp = C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.91 (d, J = 8.8 Hz, 2 H), 7.50 (d, J = 8.4 Hz, 2 H), 3.24 (t, J = 7.8 Hz, 2 H), (m, 2 H), 1.35 (s, 9 H); 13 C NMR (100 MHz, CDCl 3 ) δ 195.9, 157.4, 133.6, 128.0, (q, J = Hz), 125.7, 35.1, 31.0, 28.4 (q, J = 29.4 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ ; IR (KBr): 2965, 1683, 1605, 1336, 1142, 1100, 984 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 14 H 18 F 3 O: , found: ,4,4-trifluoro-1-phenylbutan-1-one (3b) 1, 2 White solid, 52% yield (52 mg), mp = C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.97 (d, J = 7.6 Hz, 2 H), 7.60 (t, J = 7.2 Hz, 1 H), 7.49 (t, J = 7.6 Hz, 2 H), 3.26 (t, J = 7.8 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 196.3, 136.1, 133.6, 128.8, 128.0, (q, J = Hz), 31.2 (d, J = 2.2 Hz), 28.3 (q, J = 29.6 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ ,4,4-trifluoro-1-(4-fluorophenyl)butan-1-one (3c) 1, 2 2
4 Colorless oil, 60% yield (66 mg); 1 H NMR (400 MHz, CDCl 3 ) δ 8.00 (dd, J = 8.8, 5.6 Hz, 2 H), 7.15 (t, J = 8.4 Hz, 2 H), 3.22 (t, J = 7.8 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 194.7, (d, J = Hz), (d, J = 3.0 Hz), (d, J = 9.5 Hz), (q, J = Hz), (d, J = 21.9 Hz), 31.1 (d, J = 2.2 Hz), 28.3 (q, J = 29.7 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ , (4-chlorophenyl)-4,4,4-trifluorobutan-1-one (3d) 1, 2 White solid, 72% yield (85 mg), mp = C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.91 (d, J = 8.8 Hz, 2 H), 7.46 (d, J = 8.4 Hz, 2 H), 3.22 (t, J = 7.8 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 195.1, 140.1, 134.4, 129.4, 129.1, (q, J = Hz), 31.2 (d, J = 2.1 Hz), 28.3 (q, J = 29.6 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ (4-bromophenyl)-4,4,4-trifluorobutan-1-one (3e) 1, 2 O CF 3 Br White solid, 70% yield (98 mg), mp = C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.82 (d, J = 8.4 Hz, 2 H), 7.62 (d, J = 8.0 Hz, 2 H), 3.22 (t, J = 7.8 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 195.3, 134.8, 132.1, 129.5, 128.8, (q, J = Hz), 31.2 (d, J = 3.0 Hz), 28.2 (q, J = 29.6 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ (3-bromophenyl)-4,4,4-trifluorobutan-1-one (3f) 1 Colorless oil, 62% yield (86 mg); 1 H NMR (400 MHz, CDCl 3 ) δ 8.08 (s, 1 H), 7.88 (d, J = 8.0 Hz, 1 H), 7.71 (d, J = 8.0 Hz, 1 H), 7.37 (t, J = 7.8 Hz, 1 H), 3.22 (t, J = 7.8 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 194.9, 137.7, 136.4, 131.0, 130.3, (q, J = Hz), 126.5, 123.1, 31.3 (d, J = 2.9 Hz), 28.2 (q, J = 29.7 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ (2-chlorophenyl)-4,4,4-trifluorobutan-1-one (3g) 3
5 Colorless oil, 31% yield (36 mg); 1 H NMR (400 MHz, CDCl 3 ) δ 7.51 (d, J = 7.2 Hz, 1 H), (m, 2 H), 7.35 (t, J = 6.8 Hz, 1 H), 3.24 (t, J = 7.6 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 199.3, 138.2, 132.3, 131.1, 130.7, 129.1, 127.1, (q, J = Hz), 35.4 (d, J = 2.2 Hz), 28.4 (q, J = 29.9 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ ; IR (KBr): 2966, 1690, 1582, 1331, 1142, 976 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 10 H 9 ClF 3 O: , found: ,4,4-trifluoro-1-(p-tolyl)butan-1-one (3h) 1, 2 White solid, 54% yield (58 mg), mp = C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.87 (d, J = 8.4 Hz, 2 H), 7.28 (d, J = 8.4 Hz, 2 H), 3.23 (t, J = 7.8 Hz, 2 H), (m, 2 H), 2.42 (s, 3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 195.9, 144.5, 133.7, 129.4, 128.1, (q, J = Hz), 31.0 (d, J = 2.2 Hz), 28.4 (q, J = 29.4 Hz), 21.6; 19 F NMR (376 MHz, CDCl 3 ) δ ,4,4-trifluoro-1-(4-methoxyphenyl)butan-1-one (3i) 1, 2 White solid, 55% yield (63 mg), mp = C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.94 (d, J = 8.8 Hz, 2 H), 6.94 (d, J = 8.8 Hz, 2 H), 3.87 (s, 3 H), 3.19 (t, J = 7.8 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 194.8, 163.8, 130.3, 129.2, (q, J = Hz), 113.8, 55.4, 30.7 (d, J = 2.9 Hz), 28.4 (q, J = 29.4 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ (4,4,4-trifluorobutanoyl)phenyl acetate (3j) White solid, 40% yield (52 mg), mp = C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.00 (d, J = 8.4 Hz, 2 H), 7.21 (d, J = 8.4 Hz, 2 H), 3.23 (t, J = 7.8 Hz, 2 H), (m, 2 H), 2.32 (s, 3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 195.0, 168.7, 154.7, 133.6, 129.6, (q, J = Hz), 121.9, 31.1 (d, J = 2.9 Hz), 28.3 (q, J = 29.6 Hz), 21.1; 19 F NMR (376 MHz, CDCl 3 ) δ ; IR (KBr): 2968, 1738, 1687, 1601, 1339, 1140, 1107, 981 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 12 H 12 F 3 O 3 : , found: ,4,4-trifluoro-1-(naphthalen-2-yl)butan-1-one (3k) 1, 2 4
6 White solid, 46% yield (58 mg), mp = C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.47 (s, 1 H), (m, 2 H), 7.90 (t, J = 8.6 Hz, 2 H), (m, 2 H), 3.39 (t, J = 7.8 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 196.2, 135.7, 133.4, 132.4, 129.8, 129.6, 128.7, 128.6, 127.8, (q, J = Hz), 126.9, 123.5, 31.2 (d, J = 2.9 Hz), 28.4 (q, J = 29.4 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ ,4,4-trifluoro-1-(pyridin-4-yl)butan-1-one (3l) O N CF 3 Pale yellow oil, 48% yield (48 mg); 1 H NMR (400 MHz, CDCl 3 ) δ 8.82 (d, J = 5.6 Hz, 2 H), 7.72 (d, J = 6.0 Hz, 2 H), 3.25 (t, J = 7.6 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 195.8, 151.1, 141.7, (q, J = Hz), 120.8, 31.5 (d, J = 3.0 Hz), 28.0 (q, J = 29.9 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ ; IR (KBr): 3043, 2925, 1700, 1550, 1336, 1149, 1102, 979 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 9 H 9 F 3 ON: , found: (9H-carbazol-9-yl)-4,4,4-trifluorobutan-1-one (3m) White solid, 25% yield (36 mg), mp = C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.16 (d, J = 8.4 Hz, 2 H), 7.99 (d, J = 7.6 Hz, 2 H), 7.49 (t, J = 7.8 Hz, 2 H), 7.40 (t, J = 7.4 Hz, 2 H), 3.38 (t, J = 8.0 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 169.8, 138.2, 127.5, (q, J = Hz), 126.5, 124.0, 119.9, 116.3, 32.0 (d, J = 2.9 Hz), 29.3 (q, J = 29.6 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ ; IR (KBr): 3056, 2926, 1693, 1445, 1346, 1135, 1103, 984 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 16 H 13 F 3 ON: , found: ,4,4-trifluoro-1-(2-methoxyphenyl)butan-1-one (3n) 3 O OMe Pale yellow oil, 32% yield (37 mg); 1 H NMR (400 MHz, CDCl 3 ) δ 7.76 (d, J = 7.6 Hz, 1 H), 7.49 (t, J = 8.0 Hz, 1 H), (m, 2 H), 3.93 (s, 3 H), 3.26 (t, J = 8.0 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 198.3, 158.9, 134.1, 130.5, (q, J = Hz), 126.9, 120.7, 111.5, 55.4, 36.3 (d, J = 2.2 Hz), 28.6 (q, J = 29.2 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ CF 3 1-(2,5-dimethylphenyl)-4,4,4-trifluorobutan-1-one (3o) 5
7 Colorless oil, 29% yield (33 mg); 1 H NMR (400 MHz, CDCl 3 ) δ 7.47 (s, 1 H), 7.22 (d, J = 7.6 Hz, 1 H), 7.15 (d, J = 8.0 Hz, 1 H), 3.18 (t, J = 7.6 Hz, 2 H), (m, 2 H), 2.46 (s, 3 H), 2.38 (s, 3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 199.8, 136.5, 135.5, 135.4, 132.6, 132.1, 129.1, (q, J = Hz), 33.6 (d, J = 2.2 Hz), 28.4 (q, J = 29.2 Hz), 20.9, 20.8; 19 F NMR (376 MHz, CDCl 3 ) δ ; IR (KBr): 2961, 1689, 1585, 1338, 1147, 986 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 12 H 14 F 3 O: , found: (4-(tert-butyl)phenyl)-4,4-difluorobutan-1-one (4a) White solid, 46% yield (55 mg), mp = C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.92 (d, J = 8.0 Hz, 2 H), 7.49 (d, J = 8.0 Hz, 2 H), 6.01 (tt, J = 56.8, 4.2 Hz, 1 H), 3.17 (t, J = 7.2 Hz, 2 H), (m, 2 H), 1.35 (s, 9 H); 13 C NMR (100 MHz, CDCl 3 ) δ 197.4, 157.2, 133.8, 127.9, 125.6, (t, J = Hz), 35.1, 31.0, 30.7 (t, J = 5.1 Hz), 28.4 (t, J = 21.5 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ (dt, J = 57.1, 17.7 Hz); IR (KBr): 2964, 1687, 1608, 1462, 1367, 1119, 1053 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 14 H 19 F 2 O: , found: ,4-difluoro-1-phenylbutan-1-one (4b) Colorless oil, 45% yield (41 mg); 1 H NMR (400 MHz, CDCl 3 ) δ 7.97 (d, J = 7.6 Hz, 2 H), 7.58 (t, J = 7.4 Hz, 1 H), 7.48 (t, J = 7.6 Hz, 2 H), 6.02 (tt, J = 56.8, 4.0 Hz, 1 H), 3.18 (t, J = 7.2 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 197.7, 136.3, 133.4, 128.7, 127.9, (t, J = Hz), 30.7 (t, J = 5.2 Hz), 28.3 (t, J = 21.8 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ (dt, J = 56.2, 17.9 Hz); IR (KBr): 3062, 2960, 1689, 1602, 1456, 1369, 1122, 1047 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 10 H 11 F 2 O: , found: ,4-difluoro-1-(4-fluorophenyl)butan-1-one (4c) Colorless oil, 50% yield (50 mg); 1 H NMR (400 MHz, CDCl 3 ) δ 7.99 (dd, J = 7.6, 5.6 Hz, 2 H), 7.14 (t, J = 8.2 Hz, 2 H), 6.01 (tt, J = 56.8, 4.0 Hz, 1 H), 3.15 (t, J = 7.2 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 196.1, (d, J = Hz), (d, J = 2.9 Hz), (d, J = 9.4 Hz), (t, J = Hz), (d, J = 21.9 Hz), 30.6 (t, J = 5.5 Hz), 28.3 (t, J =
8 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ (m, 1 F), (dt, J = 57.1, 18.4 Hz, 2 F); IR (KBr): 2932, 1690, 1602, 1505, 1366, 1125, 1051 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 10 H 10 F 3 O: , found: (4-chlorophenyl)-4,4-difluorobutan-1-one (4d) Colorless oil, 52% yield (56 mg); 1 H NMR (400 MHz, CDCl 3 ) δ 7.90 (d, J = 8.4 Hz, 2 H), 7.44 (d, J = 8.4 Hz, 2 H), 6.01 (tt, J = 56.8, 4.0 Hz, 1 H), 3.15 (t, J = 7.2 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 196.5, 139.8, 134.6, 129.3, 128.9, (t, J = Hz), 30.7 (t, J = 5.4 Hz), 28.2 (t, J = 21.5 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ (dt, J = 57.1, 18.4 Hz); IR (KBr): 2935, 1688, 1592, 1498, 1367, 1118, 1056 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 10 H 10 ClF 2 O: , found: (4-bromophenyl)-4,4-difluorobutan-1-one (4e) Colorless oil, 50% yield (65 mg); 1 H NMR (400 MHz, CDCl 3 ) δ 7.83 (d, J = 8.0 Hz, 2 H), 7.62 (d, J = 8.4 Hz, 2 H), 6.01 (tt, J = 56.8, 4.0 Hz, 1 H), 3.15 (t, J = 7.2 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 196.7, 135.0, 132.0, 129.5, 128.6, (t, J = Hz), 30.7 (t, J = 5.1 Hz), 28.2 (t, J = 21.9 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ (dt, J = 57.1, 17.7 Hz); IR (KBr): 2960, 1692, 1590, 1489, 1364, 1121, 1052 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 10 H 10 BrF 2 O: , found: (3-bromophenyl)-4,4-difluorobutan-1-one (4f) Colorless oil, 52% yield (68 mg); 1 H NMR (400 MHz, CDCl 3 ) δ 8.09 (s, 1 H), 7.88 (d, J = 7.6 Hz, 1 H), 7.71 (d, J = 8.0 Hz, 1 H), 7.36 (t, J = 7.8 Hz, 1 H), 6.01 (tt, J = 56.8, 4.0 Hz, 1 H), 3.16 (t, J = 7.2 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 196.4, 138.0, 136.2, 131.0, 130.3, 126.5, 123.0, (t, J = Hz), 30.9 (t, J = 5.1 Hz), 28.2 (t, J = 21.8 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ (dt, J = 56.0, 17.7 Hz); IR (KBr): 3066, 2931, 1687, 1587, 1478, 1361, 1119, 1058 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 10 H 10 BrF 2 O: , found: (2-chlorophenyl)-4,4-difluorobutan-1-one (4g) 7
9 Colorless oil, 26% yield (28 mg); 1 H NMR (400 MHz, CDCl 3 ) δ 7.49 (d, J = 7.6 Hz, 1 H), (m, 2 H), 7.34 (t, J = 7.6 Hz, 1 H), 6.00 (tt, J = 56.8, 4.2 Hz, 1 H), 3.15 (t, J = 7.2 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 200.9, 138.6, 132.0, 130.9, 130.6, 128.9, 127.0, (t, J = Hz), 35.1 (t, J = 5.1 Hz), 28.5 (t, J = 21.9 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ (dt, J = 57.1, 17.7 Hz); IR (KBr): 2963, 1691, 1588, 1369, 1121, 1055 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 10 H 10 ClF 2 O: , found: ,4-difluoro-1-(p-tolyl)butan-1-one (4h) White solid, 43% yield (42 mg), mp = C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.87 (d, J = 8.0 Hz, 2 H), 7.27 (d, J = 8.4 Hz, 2 H), 6.01 (tt, J = 56.8, 4.0 Hz, 1 H), 3.16 (t, J = 7.2 Hz, 2 H), 2.42 (s, 3 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 197.4, 144.2, 133.9, 129.3, 128.1, (t, J = Hz), 30.6 (t, J = 5.4 Hz), 28.4 (t, J = 21.5 Hz), 21.6; 19 F NMR (376 MHz, CDCl 3 ) δ (dt, J = 57.1, 17.7 Hz); IR (KBr): 2957, 1683, 1602, 1456, 1360, 1115, 1056 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 11 H 13 F 2 O: , found: ,4-difluoro-1-(4-methoxyphenyl)butan-1-one (4i) Colorless oil, 43% yield (46 mg); 1 H NMR (400 MHz, CDCl 3 ) δ 7.94 (d, J = 8.0 Hz, 2 H), 6.93 (d, J = 8.0 Hz, 2 H), 6.00 (tt, J = 56.8, 4.2 Hz, 1 H), 3.86 (s, 3 H), 3.12 (t, J = 7.2 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 196.2, 163.6, 130.2, 129.4, (t, J = Hz), 113.7, 55.4, 30.3 (t, J = 5.1 Hz), 28.4 (t, J = 21.5 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ (dt, J = 57.1, 17.8 Hz); IR (KBr): 2965, 1680, 1606, 1472, 1369, 1122, 1064 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 11 H 13 F 2 O 2 : , found: (4,4-difluorobutanoyl)phenyl acetate (4j) White solid, 30% yield (36 mg), mp = C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.00 (d, J = 8.4 Hz, 2 H), 7.20 (d, J = 8.4 Hz, 2 H), 6.01 (tt, J = 56.8, 4.0 Hz, 1 H), 3.16 (t, J = 7.2 Hz, 2 H), (m, 5 H); 13 C NMR (100 MHz, CDCl 3 ) δ 196.5, 168.7, 154.5, 133.9, 129.6, 121.9, (t, J = Hz), 30.7 (t, J = 5.1 Hz), 28.2 (t, J = 21.9 Hz), 21.0; 19 F NMR (376 MHz, CDCl 3 ) δ 8
10 (dt, J = 57.1, 17.7 Hz); IR (KBr): 2961, 1735, 1683, 1595, 1362, 1125, 1058 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 12 H 13 F 2 O 3 : , found: ,4-difluoro-1-(naphthalen-2-yl)butan-1-one (4k) White solid, 35% yield (40 mg), mp = C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.48 (s, 1 H), (m, 2 H), 7.89 (t, J = 8.0 Hz, 2 H), (m, 2 H), 6.07 (tt, J = 56.8, 4.2 Hz, 1 H), 3.32 (t, J = 7.2 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 197.6, 135.6, 133.6, 132.4, 129.7, 129.5, 128.6, 128.5, 127.7, 126.8, 123.5, (t, J = Hz), 30.8 (t, J = 5.1 Hz), 28.4 (t, J = 21.5 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ (dt, J = 57.1, 17.7 Hz); IR (KBr): 2968, 1685, 1442, 1368, 1121, 1065 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 14 H 13 F 2 O: , found: ,4-difluoro-1-(pyridin-4-yl)butan-1-one (4l) Pale yellow oil, 42% yield (38 mg); 1 H NMR (400 MHz, CDCl 3 ) δ 8.79 (d, J = 4.4 Hz, 2 H), 7.71 (d, J = 4.4 Hz, 2 H), 6.00 (tt, J = 56.8, 4.0 Hz, 1 H), 3.17 (t, J = 7.2 Hz, 2 H), (m, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 197.3, 150.9, 142.0, 120.8, (t, J = Hz), 31.0 (t, J = 5.4 Hz), 27.8 (t, J = 21.8 Hz); 19 F NMR (376 MHz, CDCl 3 ) δ (dt, J = 57.1, 17.7 Hz); IR (KBr): 3046, 2932, 1698, 1516, 1362, 1125, 1056 cm -1 ; HRMS (ESI): m/z [M + H] + calcd for C 9 H 10 F 2 ON: , found: References 1. Yang, T. P.; Li, Q.; Lin, J. H.; Xiao, J. C. Chem. Commun. 2014, 50, Park, S.; Joo, J. M.; Cho, E. J. Eur. J. Org. Chem. 2015, He, X. P.; Shu, Y. J.; Dai, J. J.; Zhang, W. M.; Feng, Y. S.; Xu, H. J. Org. Biomol. Chem. 2015, 13,
11 10
12 11
13 12
14 13
15 14
16 15
17 16
18 17
19 18
20 19
21 20
22 21
23 22
24 23
25 24
26 25
27 26
28 27
29 28
30 29
31 30
32 31
33 32
34 33
35 34
36 35
37 36
38 37
39 38
40 39
41 40
42 41
43 42
44 43
45 44
46 45
47 46
48 47
49 48
50 49
51 50
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
Διαβάστε περισσότεραCopper-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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραSupporting 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,
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραand 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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραDirect 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
Διαβάστε περισσότεραCopper-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
Διαβάστε περισσότεραSite-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,
Διαβάστε περισσότεραElectronic 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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραMetal-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:
Διαβάστε περισσότεραFirst 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
Διαβάστε περισσότεραSupporting 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,,*
Διαβάστε περισσότεραRoom 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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραFluorinative 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
Διαβάστε περισσότεραDirect 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
Διαβάστε περισσότεραVilsmeier 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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραLewis 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
Διαβάστε περισσότεραNovel 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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραHighly 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
Διαβάστε περισσότεραThe 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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραgem-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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραCopper-mediated radical cross-coupling reaction of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123) with phenols or thiophenols. Support Information
Copper-mediated radical cross-coupling reaction of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123) with phenols or thiophenols Dr. Xiao un Tang and Prof. Qing un Chen* Key Laboratory of Organofluorine Chemistry,
Διαβάστε περισσότεραAminofluorination 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,
Διαβάστε περισσότεραRegioselectivity 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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραCopper-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:
Διαβάστε περισσότεραSupplementary 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
Διαβάστε περισσότεραPhosphorus 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
Διαβάστε περισσότεραCopper-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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραElectronic 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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραIodine-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
Διαβάστε περισσότεραSupporting Information
Supporting Information Transition-metal-free Ring Expansion Reactions of Indene-1,3-dione: Synthesis of Functionalized Benzoannulated Seven-Membered Ring Compounds Qiyi Yao, Lingkai Kong, Mengdan Wang,
Διαβάστε περισσότεραFacile 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
Διαβάστε περισσότεραSupporting Information
S1 Supporting Information Synthesis of 2-Arylated Hydroxytyrosol Derivatives via Suzuki-Myaura Cross-Coupling Roberta Bernini, a Sandro Cacchi, b* Giancarlo Fabrizi, b* Eleonora Filisti b a Dipartimento
Διαβάστε περισσότεραTributylphosphine-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
Διαβάστε περισσότεραSupplementary Material
Supplementary Material Control experiments S2 Characterization data for the products S2-S7 References S8 MR spectra for the products S9-S28 S1 Control experiments 2a (99.5 mg, 0.5 mmol), I 2 (50.8 mg,
Διαβάστε περισσότεραFree 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
Διαβάστε περισσότεραEnantioselective Organocatalytic Michael Addition of Isorhodanines. to α, β-unsaturated Aldehydes
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Enantioselective Organocatalytic Michael Addition of Isorhodanines to α,
Διαβάστε περισσότεραSupporting Information. Microwave-assisted construction of triazole-linked amino acid - glucoside conjugates as novel PTP1B inhibitors
Supporting Information Microwave-assisted construction of triazole-linked amino acid - glucoside conjugates as novel PTP1B inhibitors Xiao-Peng He, abd Cui Li, d Xiao-Ping Jin, b Zhuo Song, b Hai-Lin Zhang,
Διαβάστε περισσότεραThe 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
Διαβάστε περισσότεραOxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using oxone-kx(x= Cl or Br)
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2014 Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using
Διαβάστε περισσότεραESI 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
Διαβάστε περισσότεραDivergent 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,
Διαβάστε περισσότεραSupplementary Data. Engineering, Nanjing University, Nanjing , P. R. China;
Supplementary Data Synthesis, Chemo-selective Properties of Substituted 9-Aryl-9H-fluorenes from Triarylcarbinols and Enantiomerical Kinetics of Chiral 9-Methoxy-11-(naphthalen-1-yl)-11H-benzo[a]fluorene
Διαβάστε περισσότεραRh(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,
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραSupporting Information. Synthesis and biological evaluation of 2,3-Bis(het)aryl-4-azaindoles Derivatives as protein kinases inhibitors
Supporting Information Synthesis and biological evaluation of 2,3-Bis(het)aryl-4-azaindoles Derivatives as protein kinases inhibitors Frédéric Pin, a Frédéric Buron, a Fabienne Saab, a Lionel Colliandre,
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραSynthesis and evaluation of novel aza-caged Garcinia xanthones
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Synthesis and evaluation of novel aza-caged Garcinia xanthones Xiaojin Zhang, a,1 Xiang Li, a,1 Haopeng Sun, * b Zhengyu Jiang,
Διαβάστε περισσότεραHiyama 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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραSupporting Information
Supporting Information Metal-catalyzed Stereoselective and Protecting-group-free Synthesis of 1,2-cis-Glycosides Using 4,6-Dimethoxy-1,3,5-triazin-2-yl Glycosides as Glycosyl Donors Tomonari Tanaka,* 1
Διαβάστε περισσότεραSUPPORTING 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
Διαβάστε περισσότεραSupporting 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, *
Διαβάστε περισσότεραRhodium-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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραmulticomponent synthesis of 5-amino-4-
Supporting Informartion for Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4- (arylselanyl)-1h-pyrazoles Camila S. Pires 1, Daniela H. de Oliveira 1, Maria R. B. Pontel 1, Jean
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραCatalyst-free transformation of levulinic acid into pyrrolidinones with formic acid
Catalyst-free transformation of levulinic acid into pyrrolidinones with formic acid Yawen Wei, a Chao Wang,* a Xue Jiang, a Dong Xue, a Zhao-Tie Liu, a and Jianliang Xiao* a,b a Key Laboratory of Applied
Διαβάστε περισσότεραSupporting Information. Experimental section
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Experimental section General. Anhydrous solvents were transferred by
Διαβάστε περισσότεραSupporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of. 1,2,3-Triazole Synthesis
Supporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of α-diazoketones with Various Amines: A Strategy for Catalytic Wolff 1,2,3-Triazole Synthesis Zikun Wang, a Xihe
Διαβάστε περισσότεραSupporting Information
Supporting Information Metal-Free Direct Intramolecular Carbotrifluoromethylation of Alkenes to Functionalized Trifluoromethyl Azaheterocycles Lei Li, Min Deng, Sheng-Cai Zheng, Ya-Ping Xiong, Li-Jiao
Διαβάστε περισσότεραEco-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-
Διαβάστε περισσότεραCopper-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
Διαβάστε περισσότεραSupporting 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,
Διαβάστε περισσότεραPd Catalyzed Carbonylation for the Construction of Tertiary and
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Pd Catalyzed Carbonylation for the Construction of Tertiary and Quaternary
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραChiral 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
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραLigand-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
Διαβάστε περισσότεραSupporting Information for. Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds
Supporting Information for Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds Zhongxue Fang, a Yongquan Ning, a Pengbing Mi, a Peiqiu Liao, a Xihe Bi* a,b a Department of Chemistry,
Διαβάστε περισσότεραSupporting Materials
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Carbonylative Coupling of Aryl Tosylates/triflates with Arylboronic Acids under CO Atmosphere
Διαβάστε περισσότεραCu-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
Διαβάστε περισσότεραSupporting Information
Supporting Information Selective Synthesis of xygen-containing Heterocycles via Tandem Reactions of 1,2-Allenic Ketones with Ethyl 4-Chloroacetoacetate Qiang Wang, a, b Zhouqing Xu b and Xuesen Fan a *
Διαβάστε περισσότεραKOtBu-Mediated Stereoselective Addition of Quinazolines to. Alkynes under Mild Conditions
KOtBu-Mediated Stereoselective Addition of Quinazolines to Alkynes under Mild Conditions Dan Zhao, Qi Shen, Yu-Ren Zhou, and Jian-Xin Li* State Key lab of Analytical Chemistry for Life Science, School
Διαβάστε περισσότεραSupplementary 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
Διαβάστε περισσότεραSupporting Information
1 upporting Information Rhodium(III)-Catalyzed rtho Halogenations of N-Acylsulfoximines and ynthetic Applications toward Functionalized ulfoximine Derivatives Ying Cheng, Wanrong Dong, Kanniyappan Parthasarathy,
Διαβάστε περισσότεραDiastereoselective Access to Trans-2-Substituted Cyclopentylamines
Supporting Information Diastereoselective Access to Trans-2-Substituted Cyclopentylamines Antoine Joosten, Emilie Lambert, Jean-Luc Vasse, Jan Szymoniak jean-luc.vasse@univ-reims.fr jan.szymoniak@univ-reims.fr
Διαβάστε περισσότεραCrossed Intramolecular Rauhut-Currier-Type Reactions via Dienamine Activation
Crossed Intramolecular Rauhut-Currier-Type Reactions via Dienamine Activation Eugenia Marqués-López, Raquel P. Herrera, Timo Marks, Wiebke C. Jacobs, Daniel Könning, Renata M. de Figueiredo, Mathias Christmann*
Διαβάστε περισσότεραSynthesis 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
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information A Convenient and Efficient Synthesis of Glycals by Zinc Nanoparticles
Διαβάστε περισσότεραSupporting Information
Supporting Information Regioselective Reversal in the Cyclization of 2-Diazo-3,5-dioxo-6-ynoates (ynones, ynamide): Construction of -Pyrones and 3(2H)-Furanones Starting from Identical Materials Feng Wang,
Διαβάστε περισσότεραSupporting 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).
Διαβάστε περισσότεραSupplement: Intramolecular N to N acyl migration in conformationally mobile 1 -acyl-1- systems promoted by debenzylation conditions (HCOONH 4
Cent. Eur. J. Chem. 9(5) 2011 S164-S175 DI: 10.2478/s11532-011-0082-y Central European Journal of Chemistry Supplement: Intramolecular to acyl migration in conformationally mobile 1 -acyl-1- benzyl-3,4
Διαβάστε περισσότεραSupporting 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
Διαβάστε περισσότεραSupporting Information. for. Highly Selective Hydroiodation of Alkynes Using. Iodine-Hydrophosphine Binary System
Supporting Information for Highly Selective Hydroiodation of Alkynes Using Iodine-Hydrophosphine Binary System Shin-ichi Kawaguchi and Akiya Ogawa * Department of Applied Chemistry, Graduate School of
Διαβάστε περισσότεραSupporting 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,*
Διαβάστε περισσότεραConstruction 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
Διαβάστε περισσότερα