Review of application of the I2 and dimethyl sulfoxide combined reagent system to aryl methyl ketones for diverse transformations

Abstract

The synthesis of small molecules and complex scaffolds is one of the most important topics in organic synthesis. Aryl methyl ketones, as simple and easily available materials with rich and diverse structures, can generate α-iodoaryl methyl ketones, aryl ketoaldehydes, or sulfur ylide intermediates in the I₂–dimethyl sulfoxide (DMSO) system. These molecules can be easily captured by other components in the system in situ to drive various organic unit reactions and continuous cascade transformation to realize the effective construction of C–X bonds, including C–C, C–S, C–N, and C–O bonds. The reaction system of I₂−DMSO–aryl methyl ketone has been widely used in the functionalization of the α-C–H bond of aryl methyl ketones, heterocyclic synthesis, total synthesis of natural products, and other reactions. In view of the rich research foundation and great synthesis potential of the I₂–DMSO–aryl methyl ketone reaction system, here, we review the latest progress in this field from the aspects of reaction design, the synthesis strategy, and mechanism research, with an emphasis on its synthesis application. We believe that this review will attract the interest of medical and synthetic organic chemists.