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- Title
Chemoselective Silylative Reduction of Conjugated Nitriles under Metal-Free Catalytic Conditions: β-Silyl Amines and Enamines.
- Authors
Gandhamsetty, Narasimhulu; Park, Juhyeon; Jeong, Jinseong; Park, Sung-Woo; Park, Sehoon; Chang, Sukbok
- Abstract
The B(C6F5)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(sp3)Si bond. Based on this mechanistic understanding, a preparative route to enamines was also established using bulky silanes.
- Subjects
NITRILE synthesis; AMINE synthesis; ENAMINES; SILANE compounds; HYDROSILYLATION
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 23, p6832
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201502366