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Photo-Fenton-Like (Trideutero)methylsulfonylation/Remote (Benzo)thiazolyl Migration Cascade of Unactivated Alkenes
Qing Liu1, Honglan Liu1, Ran Wang1
1Key Laboratory of Drug-Targeting and DrugDelivery System of the Education Ministry, Department of Medicinal Chemistry West China School of Pharmacy, Sichuan University, Chengdu610041, Sichuan, P. R. China.
Abstract:
We report a visible-light photocatalytic, transition-metal-free methylsulfonylation/distal (benzo)thiazolyl migration cascade of unactivated alkenes using DMSO or DMSO-d6 as methylsulfonyl or trideuteromethylsulfonyl sources. The corresponding sulfonyl radicals add selectively to the terminal alkene carbon and trigger distal migration. Mechanistic studies support hydroxyl-radical generation through a photo-Fenton-like process involving water and oxygen, without externally added hydrogen peroxide, thereby avoiding metal leaching and catalyst deactivation.
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