Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 41, Pages 13209-13213Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b08733
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- Institute for Basic Science in Korea [IBS-R010-D1]
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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.
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