Palladium-Catalyzed Direct Arylation of Selenophene

被引：45

作者：

Rampon, Daniel S. ^{[1
,2
]}

Wessjohann, Ludger A. ^{[2
]}

Schneider, Paulo H. ^{[1
]}

机构：

[1] Univ Fed Rio Grande do Sul, Inst Quim, Dept Quim Organ, BR-91501970 Porto Alegre, RS, Brazil

[2] Leibniz Inst Plant Biochem, Dept Bioorgan Chem, D-06120 Halle, Saale, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 13期

关键词：

CROSS-COUPLING REACTIONS; ZEROVALENT PALLADIUM; OXIDATIVE ADDITION; BOND FORMATION; ARYL BROMIDES; THIOPHENE; FUNCTIONALIZATION; REACTIVITY; MECHANISM; (HETERO)ARENES;

D O I：

10.1021/jo500094t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：5987 / 5992

页数：6

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