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. 2016 Oct 10;55(42):13326-13329.
doi: 10.1002/anie.201605236.

Chemoselective Reduction of Tertiary Amides to Amines Catalyzed by Triphenylborane

Debabrata Mukherjee  1 , Satoru Shirase  2 , Kazushi Mashima  2 , Jun Okuda  3
Affiliations

Chemoselective Reduction of Tertiary Amides to Amines Catalyzed by Triphenylborane

Debabrata Mukherjee et al. Angew Chem Int Ed Engl. .

Abstract

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 α-silyl amide. Preliminary studies indicate that the hydrosilylation catalyzed by BPh3 may be mechanistically different from that catalyzed by the more electrophilic B(C6 F5 )3 .

Keywords: amide reduction; chemoselectivity; hydrosilylation; triphenylborane.

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