Issue 22, 2016

Switching the regioselectivity in the copper-catalyzed synthesis of iodoimidazo[1,2-a]pyridines

Abstract

A unique copper-catalyzed binucleophilic switching of 2-aminopyridine has been developed for the regioselective synthesis of 2- and 3-iodoimidazo[1,2-a]pyridines using alkenes/alkynes as coupling partners in the presence of molecular iodine under aerobic reaction conditions. This method was also applied to the synthesis of 2-iodo-3-phenylbenzo[d]imidazo[2,1-b]thiazoles. This protocol offers an easy route towards the synthesis of 2,3-diarylimidazo[1,2-a]pyridines.

Graphical abstract: Switching the regioselectivity in the copper-catalyzed synthesis of iodoimidazo[1,2-a]pyridines

Supplementary files

Article information

Article type
Paper
Submitted
27 Mar 2016
Accepted
06 May 2016
First published
06 May 2016

Org. Biomol. Chem., 2016,14, 5073-5078

Switching the regioselectivity in the copper-catalyzed synthesis of iodoimidazo[1,2-a]pyridines

S. Samanta, S. Jana, S. Mondal, K. Monir, S. K. Chandra and A. Hajra, Org. Biomol. Chem., 2016, 14, 5073 DOI: 10.1039/C6OB00656F

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