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. Author manuscript; available in PMC: 2008 Sep 9.
Published in final edited form as: J Am Chem Soc. 2005 Dec 21;127(50):17644–17655. doi: 10.1021/ja0528580

Table 5.

Hydrosilylation of alkynyl carbonyl compounds.

graphic file with name nihms63226f17.jpg
entry alkyne cmpd silane mol% 7 product yield selectivityb
1 graphic file with name nihms63226t46.jpg 77 BnMe2SiH 0.5 78 98 >20:1
2 77 graphic file with name nihms63226t47.jpg 5 80 89 >20:1
3 graphic file with name nihms63226t48.jpg 81 (allyl)Me2SiH 4 82 81 >20:1
4 graphic file with name nihms63226t49.jpg 84 PhMe2SiH 2 85 96 >20:1
5 84 (EtO)3SiH 1 86 99 5:1
6 graphic file with name nihms63226t50.jpg 87 BnMe2SiH 1 88 67 (89)c >20:1
7 graphic file with name nihms63226t51.jpg 89 BnMe2SiH 1 90 88 7:1
8 graphic file with name nihms63226t52.jpg 91 (allyl)Me2SiH 5 92 72 15:1
9 graphic file with name nihms63226t53.jpg 93 BnMe2SiH 3 94 34 >20:1
10 graphic file with name nihms63226t54.jpg 95 BnMe2SiH 1 96 94 >20:1
a

Reactions performed using 1.2 eq. silane at 0.5 M in acetone for 30 min.

b

Ratio of β-vinylsilane: α-vinylsilane determined by analysis of crude 1H NMR. In all cases only (Z)-vinylsilane isomers were observed.

c

Yield in parenthesis is based on recovered alkyne.