cine-Silylative Ring-Opening of alpha-Methyl Azacycles Enabled by the Silylium-Induced C-N Bond Cleavage

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Described herein is the development of a borane-catalyzed cine-silylative ring-opening of alpha-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-beta-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 beta-amino elimination step.
Publisher
AMER CHEMICAL SOC
Issue Date
2020-07
Language
English
Article Type
Article
Citation

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.142, no.29, pp.12585 - 12590

ISSN
0002-7863
DOI
10.1021/jacs.0c05241
URI
http://hdl.handle.net/10203/275987
Appears in Collection
CH-Journal Papers(저널논문)
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