Table 3.
| |||||
---|---|---|---|---|---|
entry | substrate | product | R3SiCl | % yield | |
L:PPh3 | L:PCy3 | ||||
1 | Et3SiCl | 78 | 69 | ||
2 | Et3SiCl | 41 | 39 | ||
3 | Et3SiCl | 90b | 72b | ||
4 | Ph3SiCl | 63 | 60 | ||
5 | Ph3SiCl | 68c | |||
6 | Et3SiCl | N.R. |
Reaction with 1.3 equiv Et2Zn, 2.3 equiv TMSCl, 1 atm CO; 4 h for entries 1 and 2; 20 h for entries 3 and 4; 24 h for entries 5 and 6. Subseqeunt to reaction, the mixture was quenched at 0 °C with acetic acid (1.5 equiv) and TBAF (1.5 equiv) for 10 minutes and then treated with saturated Na2CO3.
Quench (footnote a) was omitted from this reaction.
A 2:1 mixture of olefin isomers was obtained.