Visible-Light-Mediated Photoredox Carbon Radical Formation from Aqueous Sulfoxonium Ylides

The visible-light-induced photoredox carbon radical for-mation from aqueous sulfoxonium ylides has been demonstrated for the first time. While direct reduction of sulfoxonium ylides by H2O efficiently generates the corresponding hydrocarbon compounds, the use of additional alkenes as radical acceptors alters the chemical reactivity to achieve alkene carboarylation of N-arylacrylamides. Mechanistic studies reveal two different reaction pathways involved in the carbon radical formation from aqueous sulfoxonium ylides resulting in reduction to release dimethyl sulfone and carboarylation to form DMSO.

Automated summary

The visible-light-induced photoredox carbon radical formation from aqueous sulfoxonium ylides has been demonstrated for the first time. Direct reduction of sulfoxonium ylides by H2O generates hydrocarbon compounds efficiently, while the use of additional alkenes as radical acceptors changes the chemical reactivity to achieve alkene carboarylation of N-arylacrylamides. Mechanistic studies reveal two different reaction pathways involved in the carbon radical formation from aqueous sulfoxonium ylides resulting in reduction to release dimethyl sulfone and carboarylation to form DMSO.