Dual Oxidation of Epoxides with a High-Valent Cu(III)–CF<sub>3</sub> Compound and DMSO to Access 1,2-Diketones
Doudou Chen, Songlin Zhang
Abstract
This study reports sequential dehydrogenation and transfer oxygenation of 1,2-diarylepoxides by high-valent phenCu(III)(CF 3 ) 3 and DMSO to produce 1,2-diketones. The Cu(III)–CF 3 compound serves as a CF 3 radical source to abstract the hydrogen atom of the epoxide ring. The resulting ether α-carbon radical undergoes ring-opening rearrangement to give a ketone α-carbon radical intermediate, which is oxygenated by DMSO with the release of Me 2 S. The combination of a Cu(III)–CF 3 compound and DMSO may be exploited to develop other novel oxidation reactions.
Topics & Concepts
DehydrogenationChemistryRing (chemistry)EpoxideMedicinal chemistryKetoneEtherPhotochemistryHydrogen atomCarbon atomCarbon fibersCatalysisOrganic chemistryMaterials scienceComposite materialAlkylComposite numberOxidative Organic Chemistry ReactionsSynthesis and Catalytic ReactionsVanadium and Halogenation Chemistry