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

Wylie S. Palmer, Keith 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
StatePublished - Oct 28 1997

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Alkynes
Palladium
alkynes
palladium
rings
synthesis
Extrusion
Metals
cycles
metals
silole
phenylacetylene
palladium chloride

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry

Cite this

Synthesis of silirenes by palladium-catalyzed transfer of silylene from siliranes to alkynes. / Palmer, Wylie S.; Woerpel, Keith.

In: Organometallics, Vol. 16, No. 22, 28.10.1997, p. 4824-4827.

Research output: Contribution to journalArticle

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