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

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The visible-light-induced photoredox carbon radical formation from aqueous sulfoxonium ylides has been demonstrated for the first time. While direct reduction of sulfoxonium ylides by H2O efficiently generates the corresponding hydrocarbon… Click to show full abstract

The visible-light-induced photoredox carbon radical formation 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.

Keywords: formation aqueous; sulfoxonium; aqueous sulfoxonium; carbon radical; radical formation; sulfoxonium ylides

Journal Title: Organic letters
Year Published: 2023

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