Chemoselective Reduction of Tertiary Amides to Amines Catalyzed by Triphenylborane | Zendy

Mukherjee Debabrata | Zendy; Shirase Satoru | Zendy; Mashima Kazushi | Zendy; Okuda Jun | Zendy

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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

Abstract 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 .

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