Iodine-catalyzed cyclization–allylation of N-allyl-2-alkynylanilines via an iodocyclization–rearrangement–deiodination sequence

Abstract

From the viewpoint of green and sustainable chemistry, metal-free cyclization-functionalization reactions of o-alkynylanilines have been developed recently. However, the applicable substrates are limited because these methods require different activation modes from those required by transition metal catalysts. Herein, we report a metal-free cyclization–allylation reaction of o-alkynylanilines catalyzed by iodine(I) species via carbo-deiodination of iodocyclized intermediates involving rearrangement of allyl groups, which is a similar mechanism to transition metal-catalysis. This method represents the first iodine-catalysis via carbo-deiodination with the rearrangement of functional groups.