Optimization of the dihydrosilylation reaction of alkynesa.
Entry | Si–H combinations | 3 | 4 | 5 |
---|---|---|---|---|
1b,c | 2a | 76% | — | <5% |
2c | 2a | 68% | — | 29% |
3 | 2a/2b = 1 : 1 | ND | 66% | 34% |
4 | 2a/2c = 1 : 1 | ND | >95% (92%) | ND |
5d | 2a/2c = 1 : 1 | ND | >95% | ND |
Reaction conditions: 1a (0.4 mmol), EtMe2SiH (2a, 0.60 mmol), Si–H (2a–2c, 0.60 mmol), B(C6F5)3 (0.04 mmol), in dichloromethane (1.0 mL). Yields were determined by NMR analysis; isolated yield in parentheses.
5 mol% B(C6F5)3.
With 3.0 equiv. of 2a.
At −40 °C.