Synthesis of azasilacyclopentenes and silanols via Huisgen cycloaddition-initiated C–H bond insertion cascades† †Electronic supplementary information (ESI) available: Full experimental details and compound characterizations, including X-ray diffraction data, are provided. CCDC 1477662–1477666 and 1477728. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc03130k Click here for additional data file. Click here for additional data file.
نویسندگان
چکیده
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 a-silyl C–H bond insertion (rather than the more common Wolff rearrangement, 1,2-shift, or bsilyl 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 postcascade transformations were also explored.
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