Catalytic Access to Bridged Sila- N-heterocycles from Piperidines via Cascade sp3 and sp2 C-Si Bond Formation

Jianbo Zhang; Sehoon Park; Sukbok Chang

doi:10.1021/jacs.8b08733

Catalytic Access to Bridged Sila- N-heterocycles from Piperidines via Cascade sp³ and sp² C-Si Bond Formation

Jianbo Zhang, Sehoon Park^*, Sukbok Chang

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

97 Scopus citations

Abstract

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) β-selective hydrosilylation of a resultant enamine intermediate, and (iii) intramolecular dehydrogenative sp² C-H silylation.

Original language	English
Pages (from-to)	13209-13213
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	140
Issue number	41
DOIs	https://doi.org/10.1021/jacs.8b08733
State	Published - 17 Oct 2018
Externally published	Yes

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title = "Catalytic Access to Bridged Sila- N-heterocycles from Piperidines via Cascade sp3 and sp2 C-Si Bond Formation",

abstract = "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) β-selective hydrosilylation of a resultant enamine intermediate, and (iii) intramolecular dehydrogenative sp2 C-H silylation.",

author = "Jianbo Zhang and Sehoon Park and Sukbok Chang",

note = "Publisher Copyright: Copyright {\textcopyright} 2018 American Chemical Society.",

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AU - Zhang, Jianbo

AU - Park, Sehoon

AU - Chang, Sukbok

PY - 2018/10/17

Y1 - 2018/10/17

N2 - 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) β-selective hydrosilylation of a resultant enamine intermediate, and (iii) intramolecular dehydrogenative sp2 C-H silylation.

AB - 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) β-selective hydrosilylation of a resultant enamine intermediate, and (iii) intramolecular dehydrogenative sp2 C-H silylation.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 41

ER -

Catalytic Access to Bridged Sila- N-heterocycles from Piperidines via Cascade sp³ and sp² C-Si Bond Formation

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