Ethynylation of pyrroles with 1-acyl-2-bromoacetylenes on alumina: a formal 脙脙脙脙脙脙inverse Sonogashira coupling脙脙脙脙脙脙

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• 作者：Trofimov ; Boris A. ; Stepanova ; Zinaida V. ; Sobenina ; Lyubov芒芒芒 N. ; Mikhaleva ; Al芒芒芒bina I. ; et. al.
• 关键词：Pyrroles ; 1-Acyl-2-bromoacetylenes ; Al₂O₃ ; 2-(Acylethynyl)pyrroles ; Sonogashira coupling
• 刊名：Tetrahedron Letters
• 出版年：2004
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：August 16, 2004
• 卷：45
• 期：34
• 页码：6513-6516
• 文件大小：271 K

摘要

Pyrroles are cross-coupled with 1-acyl-2-bromoacetylenes on the surface of Al₂O₃ at room temperature under solvent-free conditions to afford 2-(acylethynyl)pyrroles with 100%regioselectivity and in good yields, thus representing the first example of a palladium-, copper-, base-, and solvent-free (芒芒芒green芒芒芒) ethynylation of pyrroles, which can be considered a formal 芒芒芒inverse Sonogashira coupling芒芒芒. Given the interest in functionalized pyrroles and acetylenes, this new facile and environmentally friendly cross-coupling should be of significant interest for the role of acylhaloacetylenes in pyrrole and acetylene chemistry.