Table 3. Temperature Effectsa.
entry | NHC ligand | temp (°C) | 5:6 (% yield) |
---|---|---|---|
1 | IMes | rt | <2:98 (84) |
2 | IMes | 50 | <2:98 (77) |
3 | SIPr | 0 | 68:32 (81) |
4 | SIPr | rt | 83:17 (89) |
5 | SIPr | 50 | 94:6 (73) |
6 | SIPr | 95 | 98:2 (57)b |
Ni(COD)2 (0.06 mmol), NHC•HCl (0.05 mmol), and t-BuOK (0.05 mmol), were stirred with 2 mL of THF. Benzaldehyde (0.5 mmol), phenylpropyne (0.5 mmol), and silane (1.0 mmol) were combined, diluted to a total volume of 2 mL, and added to the reaction mixture via syringe drive over 1 h.
Toluene was used as the reaction solvent.