Ethynylation of pyrroles with 1-acyl-2-bromoacetylenes on alumina: a formal ‘inverse Sonogashira coupling’ |
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| Authors: | Boris A Trofimov Zinaida V Stepanova Lyubov’ N Sobenina Al’bina I Mikhaleva Igor A Ushakov |
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| Institution: | A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation |
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| Abstract: | 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 (‘green’) ethynylation of pyrroles, which can be considered a formal ‘inverse Sonogashira coupling’. 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. |
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| Keywords: | Pyrroles 1-Acyl-2-bromoacetylenes Al2O3 2-(Acylethynyl)pyrroles Sonogashira coupling |
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