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Chemoselective Reduction of Tertiary Amides to Amines Catalyzed by Triphenylborane
Author(s) -
Mukherjee Debabrata,
Shirase Satoru,
Mashima Kazushi,
Okuda Jun
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201605236
Subject(s) - chemoselectivity , amide , hydrosilylation , electrophile , chemistry , silylation , catalysis , medicinal chemistry , reduction (mathematics) , organic chemistry , combinatorial chemistry , geometry , mathematics
Triphenylborane (BPh 3 ) 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 BPh 3 may be mechanistically different from that catalyzed by the more electrophilic B(C 6 F 5 ) 3 .