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Gandhamsetty Narasimhulu
분자활성 촉매반응 연구단
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Chemoselective silylative reduction of conjugated nitriles under metal-free catalytic conditions: β-silyl amines and enamines

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Title
Chemoselective silylative reduction of conjugated nitriles under metal-free catalytic conditions: β-silyl amines and enamines
Author(s)
Narasimhulu Gandhamsetty; Juhyeon Park; Jinseong Jeong; Sung-Woo Park; Sehoon Park; Sukbok Chang
Publication Date
2015-06
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.54, no.23, pp.6832 - 6836
Publisher
WILEY-V C H VERLAG GMBH
Abstract
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. Triple whammy: The B(C6F5)3-catalyzed silylative reduction of conjugated nitriles has been developed to afford synthetically valuable β-silyl amines. Based on the mechanistic understanding, a preparative route to enamines was also established using bulky silanes. The reaction is chemoselective, has a broad scope, and proceeds under mild reaction conditions. The mechanism of the triple hydrosilylation is discussed. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
URI
https://pr.ibs.re.kr/handle/8788114/1993
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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