Manganese-catalyzed chlorosulfonylation of terminal alkene and alkyne via convergent paired electrolysis

Abstract

Convergent paired electrolysis is an energy-efficient model in organic synthesis, although the main obstacle with its use is matching properties of the intermediates generated in two electrodes. With the development of anodic-coupled electrosynthesis in three-component difunctionalization of alkene, a proposal for two-component difunctionalization of alkene and alkyne using a difunctional reagent has been raised. Herein, we develop a manganese-catalyzed, atom-transfer radical addition of the terminal aryl alkenes and alkynes with sulfonyl chlorides, in which manganese salt has the role of a chlorine atom-transfer catalyst as well as a redox mediator. This method generates analogs of chlorosulfonylated products of high regio- and stereoselectivity, which are derivatives of pharmaceutical drugs and natural products. Manganese-catalyzed electrochemical process Convergent paired electrolysis Chlorosulfonylation of alkene and alkyne Atom-transfer radical addition reaction Convergent paired electrolysis is an atom-economical and energy-efficient model in organic synthesis. Atom-transfer radical addition (ATRA) reaction is a general and facile protocol to realize α, β-functionalization of alkene and alkyne. Here, Lei et al. develop a manganese-catalyzed chlorosulfonylation of terminal alkene/yne via convergent paired electrolysis through ATRA.