American Chemical Society
ol9b00100_si_001.pdf (3.64 MB)

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

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journal contribution
posted on 2019-01-30, 18:05 authored by Xinxing Gong, Mengjiao Wang, Shengqing Ye, Jie Wu
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.