| 13%Chromat. |
With [Ir((R,R)-PPh2OCBn2C3H2NOMePh)(COD)](tetrakis(3,5-di(trifluoromethyl)phenyl)borate); hydrogen; In dichloromethane; at 50℃; under 22502.3 Torr; for 18h; |
A mixture of 2b and 2-bromovinyl boronic ester=2:1 (23 mg, 0.1 mmol) and [Ir(COD)(L8b)]BArF (17 mg, 0.01 mmol) were weighed into a glass reaction vial, placed in a Biotage Endeavour, and purged with nitrogen. Dichloromethane (3 mL) was added by injection and the reaction mixture was purged with nitrogen and hydrogen (five times) with slow stirring. The reaction was heated to 50 C under 30 bar of hydrogen with stirring for 18 h. The system was vented. The reaction crude was analyzed by GC, showing full conversion to give 5% of 4b, 86% of 3b (67% ee) and 9% of other side-products. Catalyst residue was removed by rapid filtration of the crude reaction mixture through a pipette full of silica gel, eluting with 20:1 isohexane/EtOAc. The product was isolated as a colourless oil in 50% yield, with 5% of 4b. Chromatographic and chiral purity were determined by GC method under the following conditions: Chrompack Capillary Column CP-Chirasil-Dex CB, 25 m×0.25 mm×0.25 mum; detector, 250 C; injection, 250 C; carrier gas, helium; carrier gas rate: 2.0 mL/min; column temperature: 85 C for 20 min; total run time 20 min. Retention times: 2b=6.6 min; e1-3b=6.5 min; e2-3b=6.9 min; 4b=2.3 min 1H NMR (400 MHz, CDCl3): 1.34 (12H, s), 1.72 (3H, d, J=8.0 Hz), 3.45 (1H, q, J=8.0 Hz); 13C NMR (100 MHz, CDCl3): delta 20.6, 24.5, 84.3; HRMS (ESI): [M+H]+, found: 236.1281 C8H1611BBrO2C8H1611BBrO2 requires 236.1281. This is a known compound with spectroscopic and physical properties consistent with those reported in the literature.12 |
| 13%Chromat. |
With (+)-iridium(I)-[(1,2,5,6-eta)-1,5-cyclooctadiene]-[2-(phenyl)-7-(S)-(di-tert-butylphosphinite-kappaP)-6,7-dihydro-5H-cyclopenta[b]pyridine-kappaN] tetrakis(3,5-bis(trifluoromethyl)phenyl)borate(-); hydrogen; In dichloromethane; at 50℃; under 22502.3 Torr; for 18h; |
A mixture of 2b and 2-bromovinyl boronic ester=2:1 (23 mg, 0.1 mmol) and [Ir(COD)(L8b)]BArF (17 mg, 0.01 mmol) were weighed into a glass reaction vial, placed in a Biotage Endeavour, and purged with nitrogen. Dichloromethane (3 mL) was added by injection and the reaction mixture was purged with nitrogen and hydrogen (five times) with slow stirring. The reaction was heated to 50 C under 30 bar of hydrogen with stirring for 18 h. The system was vented. The reaction crude was analyzed by GC, showing full conversion to give 5% of 4b, 86% of 3b (67% ee) and 9% of other side-products. Catalyst residue was removed by rapid filtration of the crude reaction mixture through a pipette full of silica gel, eluting with 20:1 isohexane/EtOAc. The product was isolated as a colourless oil in 50% yield, with 5% of 4b. Chromatographic and chiral purity were determined by GC method under the following conditions: Chrompack Capillary Column CP-Chirasil-Dex CB, 25 m×0.25 mm×0.25 mum; detector, 250 C; injection, 250 C; carrier gas, helium; carrier gas rate: 2.0 mL/min; column temperature: 85 C for 20 min; total run time 20 min. Retention times: 2b=6.6 min; e1-3b=6.5 min; e2-3b=6.9 min; 4b=2.3 min 1H NMR (400 MHz, CDCl3): 1.34 (12H, s), 1.72 (3H, d, J=8.0 Hz), 3.45 (1H, q, J=8.0 Hz); 13C NMR (100 MHz, CDCl3): delta 20.6, 24.5, 84.3; HRMS (ESI): [M+H]+, found: 236.1281 C8H1611BBrO2C8H1611BBrO2 requires 236.1281. This is a known compound with spectroscopic and physical properties consistent with those reported in the literature.12 |
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