Advanced Synthesis & Catalysis · 2017 · 44 citations · 65 references
Chemical EngineeringEngineeringAlkene MetathesisOxysulfonylation ReactionsIodine‐triggered Dioxygen ActivationOrganic ChemistryCatalysisRadical TrappingChemistryRedox ChemistryIodine‐triggered Aerobic OxysulfonylationChemical KineticsCatalytic Synthesis
Abstract An iodine‐triggered dioxygen activation in oxysulfonylation reactions of unactivated olefins using sulfonyl hydrazides and iodine as catalyst is reported here. In one pot, near quantitative syntheses of β‐hydroxysulfones were achieved at 70 °C, within 7 h, in acetonitrile and under aerobic conditions. A plausible mechanism is established by radical trapping and 18 O labelling experiments for the operationally simple, efficient and economically viable transformation. The direct activation of aerial oxygen under metal‐free and mild conditions is proposed for the oxysulfonylation of olefins. magnified image
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