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. 2014 Dec 22;137(2):958–963. doi: 10.1021/ja511778a

Table 3. Temperature Effectsa.

graphic file with name ja-2014-11778a_0008.jpg

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
a

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.

b

Toluene was used as the reaction solvent.