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 journalArticlepeer-review

44 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 languageEnglish
Pages (from-to)13209-13213
Number of pages5
JournalJournal of the American Chemical Society
Volume140
Issue number41
DOIs
StatePublished - 17 Oct 2018
Externally publishedYes

Fingerprint Dive into the research topics of 'Catalytic Access to Bridged Sila- N-heterocycles from Piperidines via Cascade sp<sup>3</sup> and sp<sup>2</sup> C-Si Bond Formation'. Together they form a unique fingerprint.

Cite this