A new odorless one-pot synthesis of thioesters and selenoesters promoted by Rongalite®

被引：50

作者：

Dan, Weixing ^{[1
]}

Deng, Hongjuan ^{[1
]}

Chen, Jiuxi ^{[1
]}

Liu, Miaochang ^{[1
]}

Ding, Jinchang ^{[1
,2
]}

Wu, Huayue ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

[2] Wenzhou Vocat & Tech Coll, Wenzhou 325035, Peoples R China

来源：

TETRAHEDRON | 2010年 / 66卷 / 37期

关键词：

Rongalite (R); Acylation; Disulfides; Anhydrides; Thioesters; Selenoesters; UNSYMMETRICAL DIORGANYL SELENIDES; S-S BOND; EFFICIENT SYNTHESIS; THIOL ESTERS; DIPHENYL DISELENIDE; CONVENIENT PREPARATION; SELENOL ESTERS; ACID-CHLORIDES; ACYL RADICALS; ALKYL-HALIDES;

D O I：

10.1016/j.tet.2010.07.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rongalite (R) promotes cleavage of diaryl disulfides generating chalcogenolate anions that then undergo facile acylation with anhydrides in the presence of CsF to afford thioesters (3) with good to excellent yields. By using the present protocol, 5-arylthio-5-oxopentanoic acid (4) can be facilely prepared. The important features of the methodology are broad substrate scope, simple operation, and no requirement for metal catalysts. It is noteworthy that acylations of diphenyl diselane with anhydrides are also conducted smoothly to afford selenoesters (5) in good yields under the standard conditions. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：7384 / 7388

页数：5

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