Aromatic alkenylation using electrophilic organogallium reagent generated from allenylsilane and GaCl3

Yoshiyuki Kido, Fumi Yonehara, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

Aromatic hydrocarbons are alkenylated with silylallene in the presence of GaCl3 at -90°C. Organometallic electrophiles generated from the allene and GaCl3 are the active species in this reaction. A modest level of ortho-selectivity is observed. While the silylallene reacts exclusively at the 2-position, 1,2-alkadiene reacts at the 1-position predominantly.

Original languageEnglish
Pages (from-to)827-833
Number of pages7
JournalTetrahedron
Volume57
Issue number5
DOIs
Publication statusPublished - 2001 Jan 28

Keywords

  • Allenylsilane
  • Aromatic alkenylation
  • Gallium trichloride
  • Organometallic electrophile

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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