Copper-catalyzed sulfenylation of pyrroles with disulfides or thiols: directly synthesis of sulfenyl pyrroles

被引：51

作者：

Alves, Diego ^{[1
]}

Lara, Renata G. ^{[1
]}

Contreira, Maria E. ^{[1
]}

Radatz, Catia S. ^{[1
]}

Duarte, Luis F. B. ^{[1
]}

Perin, Gelson ^{[1
]}

机构：

[1] Univ Fed Pelotas, CCQFA, LASOL, BR-96010900 Pelotas, RS, Brazil

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 26期

关键词：

Copper; Pyrroles; Disulfides; Thiols; Sulfenyl pyrroles; ARYL IODIDES; C-S; COUPLING REACTIONS; CARBON-SULFUR; EFFICIENT; POTENT; PIPERIDINE; RECEPTOR; ANALOGS; DESIGN;

D O I：

10.1016/j.tetlet.2012.04.094

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We present here the synthesis of sulfenyl pyrroles by copper-catalyzed sulfenylation of pyrroles with organic disulfides or thiols. The direct sulfenylation of pyrroles with organic disulfides has been accomplished in the presence of 3 mol % of CuI in DMSO at 110 degrees C under air atmosphere. In the other hand, sulfenylation of pyrroles with thiols were performed in the same solvent and temperature, however it is necessary 5 mol % of CuI and nitrogen atmosphere. Using these protocols we were able to produce 2-sulfenyl pyrroles in good to excellent yields and with high selectivity without use of any ligand or additive. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：3364 / 3368

页数：5

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