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Issue 10, 2017
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Synthesis of azasilacyclopentenes and silanols via Huisgen cycloaddition-initiated C–H bond insertion cascades

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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

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Publication details

The article was received on 17 Jul 2017, accepted on 21 Aug 2017 and first published on 04 Sep 2017


Article type: Edge Article
DOI: 10.1039/C7SC03130K
Citation: Chem. Sci., 2017,8, 7132-7137
  • Open access: Creative Commons BY-NC license
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    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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