Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 42, Pages 13326-13329Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201605236
Keywords
amide reduction; chemoselectivity; hydrosilylation; triphenylborane
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Funding
- Deutsche Forschungsgemeinschaft through International Research Training Group Selectivity in Chemo- and Biocatalysis
- Alexander von Humboldt Foundation
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Triphenylborane (BPh3) was found to catalyze the reduction of tertiary amides with hydrosilanes to give amines under mild condition with high chemoselectivity in the presence of ketones, esters, and imines. N,N-Dimethylacrylamide was reduced to provide the alpha-silyl amide. Preliminary studies indicate that the hydrosilylation catalyzed by BPh3 may be mechanistically different from that catalyzed by the more electrophilic B(C6F5)(3).
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