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钯催化 2-三氟甲基硫(硒)代苯并稠合杂环的串联合成。

Palladium-Catalyzed Tandem Synthesis of 2-Trifluoromethylthio(seleno)-Substituted Benzofused Heterocycles.

机构信息

State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry , Fuzhou University , Fujian 350108 , China.

出版信息

Org Lett. 2019 Aug 2;21(15):5838-5842. doi: 10.1021/acs.orglett.9b01922. Epub 2019 Jul 24.

Abstract

The tandem synthesis of 2-trifluoromethylthio(seleno)-substituted benzofurans using palladium-catalyzed conditions is reported. Trifluoromethylthio(seleno)lation of 2-(2,2-dibromovinyl)phenols with (bpy)CuSCF or [(bpy)CuSeCF] furnishes several 2-trifluoromethylthio(seleno)lated benzofurans in acceptable to good yield. Mechanistic investigations were performed to elucidate the reaction pathway, which was involved in the formation of a 2-bromobenzofuran species. The scope of this protocol was further extended to the preparation of 2-trifluoromethylthio(seleno)lated benzothiophenes and indoles.

摘要

本文报道了钯催化条件下 2-三氟甲基硫(硒)取代苯并呋喃的串联合成。(bpy)CuSCF 或 [(bpy)CuSeCF]与 2-(2,2-二溴乙烯基)苯酚的三氟甲基硫(硒)化反应以可接受至良好的产率得到了几种 2-三氟甲基硫(硒)取代的苯并呋喃。进行了机理研究以阐明反应途径,该途径涉及到 2-溴苯并呋喃物种的形成。该方案的范围进一步扩展到制备 2-三氟甲基硫(硒)取代的苯并噻吩和吲哚。

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