Efficient access to 1,3,4-trisubstituted pyrroles gold-catalysed cycloisomerization of 1,5-diynes.

Org Biomol Chem

Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education of China, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, Hunan 410081, China.

Published: February 2022

A gold-catalysed cycloisomerization of 1,5-diynes is described, which offers a selective approach to access 1,3,4-trisubstituted pyrroles. In this reaction, the cationic gold catalyst activates the ynamide moiety, initiating the cycloisomerization to produce the pyrrole core, and HO acts as an external nucleophile to trap the vinyl cationic species, thus leading to the formation of 1,3,4-trisubstituted pyrroles with high selectivity.

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Source
http://dx.doi.org/10.1039/d1ob02393dDOI Listing

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