Issue 10, 2017

Synthesis of azasilacyclopentenes and silanols via Huisgen cycloaddition-initiated C–H bond insertion cascades

Abstract

An unusual transition metal-free cascade reaction of alkynyl carbonazidates was discovered to form azasilacyclopentenes. Mild thermolysis afforded the products via a series of cyclizations, rearrangements, and an α-silyl C–H bond insertion (rather than the more common Wolff rearrangement, 1,2-shift, or β-silyl C–H insertion) to form silacyclopropanes. A mechanistic proposal for the sequence was informed by control experiments and the characterization of reaction intermediates. The substrate scope and post-cascade transformations were also explored.

Graphical abstract: Synthesis of azasilacyclopentenes and silanols via Huisgen cycloaddition-initiated C–H bond insertion cascades

Supplementary files

Article information

Article type
Edge Article
Submitted
17 Jul 2017
Accepted
21 Aug 2017
First published
04 Sep 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2017,8, 7132-7137

Synthesis of azasilacyclopentenes and silanols via Huisgen cycloaddition-initiated C–H bond insertion cascades

J. Shih, S. Jansone-Popova, C. Huynh and J. A. May, Chem. Sci., 2017, 8, 7132 DOI: 10.1039/C7SC03130K

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