Intramolecular oxysulfonylation of alkenes with the insertion of sulfur dioxide promoted by visible light is developed. The combination of 4-substituted pent-4-en-1-ols, DABCO·(SO2)2, and aryldiazonium tetrafluoroborates under mild conditions in the presence of a photocatalyst provides sulfonated 2,2-disubstituted tetrahydrofurans in moderate to good yields. Moreover, this protocol can be further extended to 5-phenylhex-5-en-1-ol and [2-(prop-1-en-2-yl)phenyl]methanol for the construction of sulfonyl-containing tetrahydropyran and 1,3-dihydroisobenzofuran derivatives. Preliminary mechanistic studies show that the arylsulfonyl radical is the key intermediate in the reaction process.
- This article is part of the themed collection: Celebrating the 90th birthday of Professor Lu Xiyan