<scp>Cu‐Catalyzed</scp> Cascade Cyclization of Ketoxime Acetates and Alkynals Enabling Synthesis of Acylpyrroles
Zhenhua Xu, Ning Xian, Hongbiao Chen, Guo‐Jun Deng, Huawen Huang
Abstract
Main observation and conclusion A facile copper‐based catalytic system has been developed to enable efficient cyclization of methylketoximes and alkynals. This protocol provides a viable entry to synthetically and pharmaceutically useful 2‐acylpyrroles with a broad range of compatible functionalities. Mechanistically, a key acyl migration is probably involved that leads to the formation of N ‐acyl pyrroles or otherwise NH pyrroles by further hydrolysis. More importantly, the present reaction system also gives an opportunity to realize three‐component pyrrole assembly by simple addition of carboxylic acid.
Topics & Concepts
ChemistryCatalysisCombinatorial chemistryHydrolysisPyrroleCascadeEster hydrolysisOrganic chemistryChromatographySynthesis and Characterization of PyrrolesCatalytic C–H Functionalization MethodsCarbon dioxide utilization in catalysis