Gold-catalyzed cyclization of (ortho-alkynylphenylthio)silanes: Intramolecular capture of the vinyl-au intermediate by the silicon electrophile

Itaru Nakamura, Takuma Sato, Masahiro Terada, Yoshinori Yamamoto

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114 Citations (Scopus)

Abstract

The gold-catalyzed cyclization of (ortho-alkynylphenylthio)silanes 1 produced the corresponding 3-silylbenzo[b]thiophenes 2 in good to excellent yields. For example, the reaction of [2-(1-pentynyl)phenylthio] triisopropylsilane 1a, [2-(p-anisylethynyl)phenylthio]triisopropylsilane 1e, and [2-(phenylethynyl)phenylthio]triisopropylsilane 1g in the presence of 2 mol % of AuCl in toluene at 45°C gave 2a, 2e, and 2g in 98, 99, and 97% yields, respectively. This reaction proceeds through intramolecular capture of the vinyl-Au intermediate by the silicon electrophile, so-called silyldemetalation.

Original languageEnglish
Pages (from-to)4081-4083
Number of pages3
JournalOrganic letters
Volume9
Issue number20
DOIs
Publication statusPublished - 2007 Sep 27

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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