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. Author manuscript; available in PMC: 2017 Apr 13.
Published in final edited form as: J Am Chem Soc. 2016 Mar 30;138(14):4962–4971. doi: 10.1021/jacs.6b02032

Table 2.

Effects of 6 on the catalyst loading of the HAT hydrogenation.a

graphic file with name nihms781737u3.jpg
entry silane conditions conv/yield (%)b d.r.
1 3 i-PrOH, 10 mol% 94/89 7.5
2 3 i-PrOH, 1 mol% 61/53 8.3
3 3 i-PrOH, 0.1 mol% 27/28 9.2
4 3 hexane, 10 mol% 35/17 9.5
5 6 i-PrOH, 10 mol% 99/98 4.1
6 6 i-PrOH, 1 mol% 100/87 5.5
7 6 hexane, 10 mol% 94/93 5.2
8 6 hexane, 1 mol% 100/97 6.3
9 6 hexane, 0.1 mol% 100/91 6.6
10 6 hexane, 0.05 mol%c 100/98 6.6
11 6 hexane, 0.02 mol%c 48/15 6.2
12 11 i-PrOH, 10 mol% 98/86 5.3
13 11 hexane, 10 mol% 49/33 5.9
a

Reactions performed with 1 equiv. of PhSiH3, 1.5 equiv. of Ph(i-PrO)SiH2 or 3 equiv. of Ph(i-PrO)2SiH.

b

Determined by GC-FID using 1 equiv. of decane as internal standard.

c

Reaction time 13 h.