Diphenyl Disulfone

Hydrosulfonylation of Unactivated Alkenes Involving Sulfonyl Radical Generation via Photocatalytic Activation of Symmetrical Disulfones by an Energy Transfer Mimicry

“…In contrast, the fully oxidized disulfide analogues, i.e., disulfones (d), are benchstable and hydrolytically resistant solids that can be obtained from disulfides or thiosulfonates via oxidation. 4,9,10 They are scarcely investigated as radical precursors in organic synthesis. Homolytical cleavage at elevated temperature 11 or with harsh UV-C light, 12 and has been exploited in the photopolymerization of styrene, the isomerization of methylenecyclopentane, and the deprotection of methallyl, prenyl, and methylprenyl ethers.…”

“…Sulfinylsulfones are rather unstable in air and oxidize toward the corresponding sulfonic anhydride within hours, while under an inert atmosphere, they decompose within days to the corresponding thiosulfonate and sulfonic acid. In contrast, the fully oxidized disulfide analogues, i.e., disulfones ( d ), are bench-stable and hydrolytically resistant solids that can be obtained from disulfides or thiosulfonates via oxidation. ,, They are scarcely investigated as radical precursors in organic synthesis. Homolytical cleavage at elevated temperature or with harsh UV-C light, which generates two sulfonyl radicals, is known and has been exploited in the photopolymerization of styrene, the isomerization of methylenecyclopentane, and the deprotection of methallyl, prenyl, and methylprenyl ethers. , Interestingly, in all these examples, disulfones were catalytically added to the reaction mixture to act as initiator or HAT catalyst and they are still unexplored as stoichiometric sulfonyl radical source for the synthesis of sulfonyl-containing products.…”

“…In contrast, the fully oxidized disulfide analogues, i.e., disulfones ( d ), are bench-stable and hydrolytically resistant solids that can be obtained from disulfides or thiosulfonates via oxidation. ,, They are scarcely investigated as radical precursors in organic synthesis. Homolytical cleavage at elevated temperature or with harsh UV-C light, which generates two sulfonyl radicals, is known and has been exploited in the photopolymerization of styrene, the isomerization of methylenecyclopentane, and the deprotection of methallyl, prenyl, and methylprenyl ethers. , Interestingly, in all these examples, disulfones were catalytically added to the reaction mixture to act as initiator or HAT catalyst and they are still unexplored as stoichiometric sulfonyl radical source for the synthesis of sulfonyl-containing products. Moreover, activation of symmetrical disulfones by visible light photocatalysis is unknown, although they have the potential of generating two identical sulfonyl radicals in a mild manner without byproduct production.…”