Aliphatic thioacetate deprotection using catalytic tetrabutylammonium. cyanide

被引：27

作者：

Holmes, BT ^{[1
]}

Snow, AW ^{[1
]}

机构：

[1] USN, Res Lab, Dept Chem, Washington, DC 20375 USA

来源：

TETRAHEDRON | 2005年 / 61卷 / 52期

关键词：

thioacetate; deprotection; tetrabutylammoniurn cyanide; thiol;

D O I：

10.1016/j.tet.2005.09.092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of thiol-functionalized organic compounds were selected to analyze the scope and efficiency of a new thioacetate deprotection method using catalytic tetrabutylammonium cyanide (TBACN) to effect the transformation of a thioacetate group to a free thiol in the presence of a protic solvent. Particularly attractive are the mild reaction and workup conditions, reduced byproduct formation typically seen using literature methods and yields of greater than 80% for the free aliphatic thiols. This method is effective on aliphatic thiols with trityl, benzyl, p-halo-benzyl, phenethyl, phenoxyethyl, and cyclohexylethyl structural moieties, but it is not effective with thiophenols. Published by Elsevier Ltd.

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页码：12339 / 12342

页数：4

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