Catalytic Access to Bridged Sila-N-heterocycles from Piperidines via Cascade sp(3) and sp(2) C-Si Bond Formation

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Described herein is the development of an unprecedented route to bridged sila-N-heterocycles via B(C6F5)(3)-catalyzed cascade silylation of N-aryl piperidines with hydrosilanes. Mechanistic studies indicated that an outer-sphere ionic path is operative to involve three sequential catalytic steps having N-silyl piperidinium borohydride as a resting species: (i) dehydrogenation of the piperidine ring, (ii) beta-selective hydrosilylation of a resultant enamine intermediate, and (iii) intramolecular dehydrogenative sp(2) C-H silylation.
Publisher
AMER CHEMICAL SOC
Issue Date
2018-10
Language
English
Article Type
Article
Keywords

H SILYLATION; B(C6F5)(3)-CATALYZED HYDROSILYLATION; AROMATIC HETEROCYCLES; REDUCTION; HYDROSILANES; AMINES; ACTIVATION; INHIBITORS; MECHANISM; SILICON

Citation

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.140, no.41, pp.13209 - 13213

ISSN
0002-7863
DOI
10.1021/jacs.8b08733
URI
http://hdl.handle.net/10203/246696
Appears in Collection
CH-Journal Papers(저널논문)
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