Herein, we report a mechanochemical-driven, nonphotochemical electron donor–acceptor (EDA)-complex strategy for the synthesis of thioethers via site-selective C–H functionalization using aryl (DMIX)iodonium salts (acceptor) and potassium thiolate salts (donor), providing a straightforward approach toward C–S bond formation under ball milling conditions. This protocol enables rapid access to thioethers via site-selective C–H functionalization from a wide range of aromatic and heteroaromatic substrates, including pharmaceutical derivatives, as well as diverse alkyl, aryl, and heteroaryl potassium thiolate salts, affording the desired products with excellent efficiency and regioselectivity. Mechanistic investigations indicated the formation of an EDA complex in the reaction medium and the involvement of a radical mechanistic pathway for the product formation. Overall, the dual combination of mechanochemistry with nonphotochemical EDA-complex activation provides a versatile platform for thioether synthesis with potential applications in medicinal chemistry and related areas.
Patel et al. (Sat,) studied this question.
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