Efficient Generation of C–S Bonds via a By‐Product‐Promoted Selective Coupling of Alcohols, Organic Halides, and Thiourea

Abstract

AbstractA metal‐ and base‐free three‐component coupling of alcohols, heteroaryl halides, and thiourea has been developed for direct and selective synthesis of heteroaryl thioethers. This method can be easily scaled up to the gram scale and extended to dialkyl thioethers, heteroaryl selenides, benzothiazoles, and some antimycobacterially‐active thioethers. Mechanistic studies revealed that a by‐product‐promoted in situ C–O activation of alcohols to more reactive alkyl halides and slow release of the thiol and alkyl halide intermediates are the key to the high selectivity and success of the reaction.magnified image