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.