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

Table 2. Concentration Effectsa.

graphic file with name ja-2014-11778a_0007.jpg

entry silane (equiv) concb (M) 5:6 (% yield)
1 Et3SiH (2.0) 0.125 58:42 (65)
2 Et3SiH (10.0) 0.125 58:42 (32)
3 (i-Pr)3SiH (1.1) 0.125 95:5 (57)
4 (i-Pr)3SiH (2.0) 0.125 83:17 (89)
5 (i-Pr)3SiH (10.0) 0.125 68:32 (93)
6 (i-Pr)3SiH (2.0) 0.0125c >98:2 (82)
a

Ni(COD)2 (0.06 mmol), SIPr·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 were combined, diluted to a total volume of 2 mL, and added to the reaction mixture via syringe drive over 1 h at rt.

b

Concentration refers to the final molarity of the aldehyde and alkyne starting components.

c

The catalyst was prepared in 38 mL of THF.