Gold-catalyzed etherification and friedel - Crafts alkylation using ortho-alkynylbenzoic acid alkyl ester as an efficient alkylating agent

Naoki Asao, Haruo Aikawa, Sakie Tago, Kazuteru Umetsu

Research output: Contribution to journalArticlepeer-review

59 Citations (Scopus)

Abstract

A gold-catalyzed alkylation of alcohols and aromatic compounds is described. The reaction of ortho-alkynylbenzoic acid alkyl esters with alcohols or aromatic compounds occurs in the presence of catalytic amounts of Ph 3PAuCl and AgOTf under mild conditions to produce corresponding ethers or Friedel-Crafts alkylation products in good to high yields. The reaction likely proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack of alcohols or aromatic compounds.

Original languageEnglish
Pages (from-to)4299-4302
Number of pages4
JournalOrganic letters
Volume9
Issue number21
DOIs
Publication statusPublished - 2007 Oct 11
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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