Tetrahedron

Gold-catalyzed substitution reaction with ortho-alkynylbenzoic acid alkyl ester as an efficient alkylating agent

H Aikawa, S Tago, K Umetsu, N Haginiwa, N Asao

Index: Aikawa, Haruo; Tago, Sakie; Umetsu, Kazuteru; Haginiwa, Naomichi; Asao, Naoki Tetrahedron, 2009 , vol. 65, # 9 p. 1774 - 1784

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Citation Number: 38

Abstract

ortho-Alkynylbenzoic acid alkyl esters behave as alkylating agents in combination with gold catalysts. The reaction with alcohols occurs smoothly in the presence of catalytic amounts of Ph3PAuCl and AgOTf under mild conditions to produce the corresponding ether products in high yields. The protocol is also useful for Friedel–Crafts alkylation and N-alkylation of sulfonamides. The reaction likely proceeds through the gold-induced in situ construction ...

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