Gold-catalyzed etherification and Friedel-Crafts alkylation using ortho-alkynylbenzoic acid alkyl ester as an efficient alkylating agent.
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 Ph3PAuCl 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.
Asao
Naoki
N
Department of Chemistry, and Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. asao@mail.tains.tohoku.ac.jp
Aikawa
Haruo
H
Tago
Sakie
S
Umetsu
Kazuteru
K