Cyclocarbonylation-Iodination of terminal alkynes with ketones and ICl via 1,2-migration

Abstract

A simple, three-component, one-pot, room-temperature reaction of cyclocarbonylation-iodination is developed from terminal alkynes, ketones, and ICl. The reaction proceeds through the formation of 3°-propargyl alcohols and a subsequent 1,2-shift lead to the formation of β-iodo-α,β-unsaturated cyclic and acyclic ketones in good yields. In the case of cyclic ketones, the products are obtained with ring expansion.