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Zhang, Jianbo
분자활성 촉매반응 연구단
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cine-Silylative Ring-Opening of α-Methyl Azacycles Enabled by the Silylium-Induced C-N Bond Cleavage

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Title
cine-Silylative Ring-Opening of α-Methyl Azacycles Enabled by the Silylium-Induced C-N Bond Cleavage
Author(s)
Jianbo Zhang; Sukbok Chang
Subject
FRUSTRATED LEWIS PAIRS, ; NITROGEN, ; SILICON, ; FUNCTIONALIZATION, ; ACTIVATION, ; REDUCTION, ; ROUTE, ; HYDROSILYLATION
Publication Date
2020-07
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.142, no.29, pp.12585 - 12590
Publisher
AMER CHEMICAL SOC
Abstract
Described herein is the development of a borane-catalyzed cine-silylative ring-opening of α-methyl azacycles. This transformation involves four-step cascade processes: (i) exo-dehydrogenation of alicyclic amine, (ii) hydrosilylation of the resultant enamine, (iii) silylium-induced cis-β-amino elimination to open the ring skeleton, and (iv) hydrosilylation of the terminal olefin. The present borane catalysis also works efficiently for the C-N bond cleavage of acyclic tertiary amines. On the basis of experimental and computational studies, the silicon atom was elucidated to play a pivotal role in the β-amino elimination step © 2020 American Chemical Society
URI
https://pr.ibs.re.kr/handle/8788114/7767
DOI
10.1021/jacs.0c05241
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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