Iodine(iii)-mediated dehydroaromatization of cyclohexanones with primary amines and CD3SSO3Na to access ortho-SCD3 anilines†

Abstract

Iodine(iii)-mediated dehydroaromatization of cyclohexanones with primary amines and CD₃SSO₃Na has been developed, providing direct access to ortho-SCD₃ anilines with the formation of C–N and C–S bonds. Detailed mechanism studies indicate that hypervalent iodine(iii) plays dual roles as an efficient mediator and an oxidant, and the continuously generated α-acetoxylated ketones and α-SCD₃ ketones are the key intermediates in the current three-component reactions. The present transformations demonstrate excellent chemo-selectivity, and only employ an iodine(iii) reagent as a stoichiometric mediator, making the strategy applicable for late-stage modification of numerous pharmaceuticals.