Issue 43, 2020

Copper and manganese co-mediated cascade aza-Michael addition/cyclization and azidation of 1,3-enynes: regioselective synthesis of fully substituted azido pyrroles

Abstract

An efficient Cu and Mn co-mediated aerobic oxidative cyclization and azidation reaction of 1,3-enynes with amines and trimethylsilyl azide (TMSN3) for the synthesis of fully substituted azido pyrroles has been developed. The three-component reaction has the characteristics of high regioselectivity, wide substrate scope, and mild reaction conditions. A preliminary mechanism for this transformation is proposed.

Graphical abstract: Copper and manganese co-mediated cascade aza-Michael addition/cyclization and azidation of 1,3-enynes: regioselective synthesis of fully substituted azido pyrroles

Supplementary files

Article information

Article type
Paper
Submitted
19 Sep 2020
Accepted
20 Oct 2020
First published
20 Oct 2020

Org. Biomol. Chem., 2020,18, 8908-8915

Copper and manganese co-mediated cascade aza-Michael addition/cyclization and azidation of 1,3-enynes: regioselective synthesis of fully substituted azido pyrroles

J. Ge, Q. Ding, M. Yang, T. He and Y. Peng, Org. Biomol. Chem., 2020, 18, 8908 DOI: 10.1039/D0OB01927E

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