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

被引：46

作者：

Aikawa, Haruo ^{[1
]}

Tago, Sakie ^{[1
]}

Umetsu, Kazuteru ^{[1
]}

Haginiwa, Naomichi ^{[1
]}

Asao, Naoki ^{[1
,2
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

[2] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON | 2009年 / 65卷 / 09期

关键词：

Gold catalyst; Substitution; Etherification; Friedel-Crafts alkylation; N-Alkylation of sulfonamide; EARTH-METAL CATALYSTS; INTRAMOLECULAR CARBOALKOXYLATION; SOLID SUPERACIDS; NAFION-H; C-N; ALCOHOLS; ETHERS; COMPLEXES; ACTIVATION; ROUTE;

D O I：

10.1016/j.tet.2008.12.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 of leaving groups and Subsequent nucleophilic attack of nucleophiles, such as alcohols, aromatic compounds, and sulfonamides. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1774 / 1784

页数：11

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