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Chemoselective Reduction of Tertiary Amides to Amines Catalyzed by Triphenylborane

Debabrata Mukherjee, Satoru Shirase, Kazushi Mashima, Jun Okuda

Angew Chem Int Ed Engl. 2016 Oct 10;55(42):13326-13329.

PMID: 27650798

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 .

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP960714-B Triphenylborane Triphenylborane 960-71-4 Price
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