Synthesis of 3-(Methylsulfonyl)benzo[ b]thiophenes from Methyl(2-alkynylphenyl)sulfanes and Sodium Metabisulfite via a Radical Relay Strategy.

A radical relay strategy for the generation of 3-(methylsulfonyl)benzo[ b]thiophenes through a reaction of methyl(2-alkynylphenyl)sulfanes with sodium metabisulfite in the presence of a photocatalyst under visible light irradiation is developed. This photoinduced sulfonylation proceeds efficiently under mild conditions by using a catalytic amount of sodium methylsulfinate as an initiator. During the reaction process, the methyl radical generated in situ is the key intermediate, which undergoes a radical relay with the combination of sulfur dioxide to afford methylsulfonyl-containing compounds.