钯催化的硒吩直接芳基化反应。

Palladium-catalyzed direct arylation of selenophene.

作者信息

Rampon Daniel S, Wessjohann Ludger A, Schneider Paulo H

机构信息

Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio Grande do Sul , UFRGS, 91501-970 Porto Alegre-RS, Brazil.

出版信息

J Org Chem. 2014 Jul 3;79(13):5987-92. doi: 10.1021/jo500094t. Epub 2014 Jun 16.

DOI:10.1021/jo500094t

PMID:24893620

Abstract

An efficient and convenient method was developed for the regioselective formation of 2-aryl- or 2,5-diarylselenophenes via a palladium-catalyzed direct arylation. This protocol is suitable for a wide range of aryl halides containing different functional groups. The 2-arylated substrates can undergo an additional regioselective direct arylation event furnishing symmetrical or unsymmetrical 2,5-diaryl selenophenes in good yield. Competition experiments and the role of the acid additive are in agreement with a concerted metalation deprotonation (CMD) pathway.

摘要

通过钯催化的直接芳基化反应，开发了一种高效便捷的方法用于区域选择性地形成2-芳基或2,5-二芳基硒吩。该方法适用于多种含有不同官能团的芳基卤化物。2-芳基化的底物可以进行额外的区域选择性直接芳基化反应，以良好的产率得到对称或不对称的2,5-二芳基硒吩。竞争实验和酸添加剂的作用与协同金属化去质子化（CMD）途径一致。