Chemoselective Silylative Reduction of Conjugated Nitriles under Metal-Free Catalytic Conditions: -Silyl Amines and Enamines

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The B(C6F5)(3)-catalyzed silylative reduction of conjugated nitriles has been developed to afford synthetically valuable -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 -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.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2015-06
Language
English
Article Type
Article
Keywords

SILICON-CONTAINING COMPOUNDS; B(C6F5)(3)-CATALYZED HYDROSILYLATION; ORGANIC-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; PINCER COMPLEX; ENOL ETHERS; H BONDS; HYDROGENATION; ALCOHOLS

Citation

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.54, no.23, pp.6832 - 6836

ISSN
1433-7851
DOI
10.1002/anie.201502366
URI
http://hdl.handle.net/10203/199456
Appears in Collection
CH-Journal Papers(저널논문)
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