Gold (III)-catalyzed direct nucleophilic substitution of propargylic alcohols

被引：128

作者：

Georgy, Marie ^{[2
]}

Boucard, Valerie ^{[2
]}

Debleds, Olivier ^{[1
]}

Dal Zotto, Christophe ^{[1
]}

Campagne, Jean-Marc ^{[1
]}

机构：

[1] CNRS, Inst Charles Gerhardt Montpellier, ENSCM, UMR 5253,UM2 UM1, F-34296 Montpellier, France

[2] Inst Chim Subst Nat, UPR 2301, F-91198 Gif Sur Yvette, France

来源：

TETRAHEDRON | 2009年 / 65卷 / 09期

关键词：

CATALYZED DIRECT AMINATION; BOND-FORMING REACTIONS; 1,3-DICARBONYL DERIVATIVES; KETONES; ALKYNYLATION; CATIONS; ISOMERIZATION; BENZYLATION; ALLYLATION; 1,5-ENYNES;

D O I：

10.1016/j.tet.2008.12.051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Gold-catalyzed nucleophilic substitution of propargylic alcohols with various nucleophiles (allylsilane, electron-rich aromatics, alcohols. thiols, hydrides, 1,3-dicarbonyl derivatives, sulfonamides) is described under very mild conditions (room temperature in dichloromethane). Preliminary mechanistic investigations suggest a mechanism through a carbocation intermediate. Nucleophilic substitutions on allylic and benzylic alcohols are also described. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1758 / 1766

页数：9

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