Visible Light-Driven, Persulfate-Mediated Hydrocarboxylation of Vinylsulfones

We report a visible light-mediated approach for the radical hydrocarboxylation of vinylsulfone derivatives. Using cheap and easily accessible sodium formate as C1-source and K2S2O8 as reagent, a set of vinylsulfone substrates could be efficiently hydrocarboxylated in aqueous medium without any additional catalyst or reagent; and the concept could be also applied for direct hydroacylations, hydroalkylations and hydrophosphorylations. The control experiments clearly indicated that the reaction proceeds via radical mechanism without the generation of electron donor-acceptor (EDA) complexes; supporting the working model of K2S2O8-initiated in situ formation of CO2 radical anion.

Automated summary

A visible light-mediated approach for radical hydrocarboxylation of vinylsulfone derivatives is reported. Vinylsulfone substrates can be efficiently hydrocarboxylated in aqueous medium using cheap and accessible sodium formate as a C1 source and K2S2O8 as a reagent, without any additional catalyst or reagent. Control experiments demonstrate that the reaction proceeds via a radical mechanism, supported by the working model of K2S2O8-initiated in situ formation of CO2 radical anion.