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Chemoselective Silylative Reduction of Conjugated Nitriles under Metal‐Free Catalytic Conditions: β‐Silyl Amines and Enamines
Author(s) -
Gandhamsetty Narasimhulu,
Park Juhyeon,
Jeong Jinseong,
Park SungWoo,
Park Sehoon,
Chang Sukbok
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201502366
Subject(s) - silylation , conjugated system , chemistry , silanes , enamine , hydrosilylation , nitrile , amine gas treating , catalysis , organic chemistry , combinatorial chemistry , silane , polymer
The B(C 6 F 5 ) 3 ‐catalyzed silylative reduction of conjugated nitriles has been developed to afford synthetically valuable β‐silyl amines. The reaction is chemoselective and proceeds under mild conditions. Mechanistic elucidation indicates that it proceeds by rapid double hydrosilylation of the conjugated nitrile to an enamine intermediate which is subsequently reduced to the β‐silyl amine, thus forming a new C(sp 3 )Si bond. Based on this mechanistic understanding, a preparative route to enamines was also established using bulky silanes.