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

Table 1. Ligand and Silane Structural Effects^a.

entry	ligand	R₃SiH	5:6 (% yield)
1	IMes	Et₃SiH	<2:98 (84)
2	IMes	(i-Pr)₃SiH	<2:98 (83)
3	SIMes	Et₃SiH	4:96^b
4	SIMes	(i-Pr)₃SiH	4:96^b
5	IPr	Et₃SiH	44:56^b
6	IPr	(i-Pr)₃SiH	56:44^b
7	SIPr	Et₃SiH	58:42 (65)
8	SIPr	t-BuMe₂SiH	60:40 (83)
9	SIPr	t-BuPh₂SiH	77:23 (86)
10	SIPr	(i-Pr)₃SiH	83:17 (89)
11	SIPr	(t-Bu)₂MeSiH	>98:2 (61)

Ni(COD)₂ (0.06 mmol), ligand·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 at rt. IMes·Cl = 1,3-bis(mesityl)imidazolium chloride; SIMes·HCl = 1,3-bis(mesityl)-4,5-dihydroimidazolium chloride; IPr·HCl = 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride; SIPr·HCl = 1,3-bis(2,6-diisopropyl-phenyl)-4,5-dihydroimidazolium chloride.

Isolated yield not determined.

Table 1. Ligand and Silane Structural Effectsa.

Table 1. Ligand and Silane Structural Effects^a.