GaCl3-catalyzed ortho-ethynylation of phenols

Katsumi Kobayashi, Mieko Arisawa, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

124 Citations (Scopus)

Abstract

Phenols are ethynylated at the ortho position with silylated chloroethyne in the presence of a catalytic amount of GaCl3 and lithium phenoxide. The lithium salt is essential for the catalysis, and addition of 2,6-di(tert-butyl)-4-methylpyridine inhibits desilylation and hydration of the products. The reaction can be applied to various substituted phenols giving the ortho-ethynylated products in high yields, and the turnover numbers based on GaCl3 are between 8 and 10. The reaction mechanism involves addition of in situ formed phenoxygallium to the haloethyne followed by the elimination of GaCl3.

Original languageEnglish
Pages (from-to)8528-8529
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number29
DOIs
Publication statusPublished - 2002 Jul 24

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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