Synthesis of silirenes by palladium-catalyzed transfer of silylene from siliranes to alkynes

Wylie S. Palmer, K. A. Woerpel

Research output: Contribution to journalArticle

Abstract

Palladium-catalyzed reactions of cis-1,1-di-tert-butyl-2,3-dimethylsilirane with disubstituted alkynes produced thermally stable silirenes in high yields (81-86%). Alkyl-, aryl-, trimethylsilyl-, and heteroatom-substituted alkynes were employed. The silirenes reacted with phenylacetylene and <3 mol % of PdCl2(PPh3)2 to produce trisubstituted siloles. A common catalytic cycle involving palladasilacyclobutene accounts for both the formation of silirene and the trisubstituted silole. The palladium-catalyzed extrusion of silylene effectively transfers silylene from one strained ring (a silirane) to form another strained ring (a silirene) and represents an unusual metal-mediated process.

Original languageEnglish (US)
Pages (from-to)4824-4827
Number of pages4
JournalOrganometallics
Volume16
Issue number22
DOIs
StatePublished - Oct 28 1997

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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