Ph2S2-CaH2 in N-methyl-2-pyrrolidone as an efficient protocol for chemoselective cleavage of aryl alkyl ethers

被引：12

作者：

Gavande, NS ^{[1
]}

Kundu, S ^{[1
]}

Badgujar, NS ^{[1
]}

Kaur, G ^{[1
]}

Chakraborti, AK ^{[1
]}

机构：

[1] NIPER, Dept Med Chem, Nagar 160062, Punjab, India

来源：

TETRAHEDRON | 2006年 / 62卷 / 17期

关键词：

cleavage; diphenyl disulfide; calcium hydride; chemoselective; thiophenolate anion;

D O I：

10.1016/j.tet.2006.02.013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

CaH2 was been found, for the first time, as a mild reducing agent to generate thiophenolate anion from Ph2S2 in N-methyl-2-pyrrolidone (NMP) for deprotection of aryl alkyl ethers. Excellent chemoselctivity was observed for substrates having chloro, and nitro groups without displacement of the chlorine atom and the nitro group. Selective ether cleavage took place in the presence of alpha,beta-unsaturated carbonyl and nitro groups without reduction and conjugate addition (to the alpha, beta-unsaturated carbonyl group). (c) 2006 Elsevier Ltd. All rights reserved.

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页码：4201 / 4204

页数：4

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