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Controlling Selectivity in Shuttle Hetero‐difunctionalization Reactions: Electrochemical Transfer Halo‐thiolation of Alkynes

Shuttle hetero-difunctionalization reaction, in which two chemically distinct functional groups are transferred between two molecules, has long been an unmet goal due to the daunting challenges in controlling the chemo-, regio-, and stereoselectivity. Herein, we disclose an electrochemistry enabled shuttle reaction ( e -shuttle) to selectively transfer one RS ‒ and one X ‒ group between β-halosulfide and unsaturated hydrocarbons via a consecutive paired electrolysis mechanism. The preferential anodic oxidation of one anion over the other, which is controlled by their distinct redox potentials, plays a pivotal role in controlling the high chemoselectivity of the process. This easily scalable methodology enables the construction of a myriad of densely functionalized β-halo alkenyl sulfides in unprecedented chemo-, regio-, and stereoselectivity using benign surrogates, e.g., 2-bromoethyl sulfide, avoiding the handling of corrosive and oxidative RS–Br reagents. In a broader context, these results open up new strategies for selective shuttle difunctionalization reactions.

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