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Direct Photoredox‐Catalyzed Reductive Difluoromethylation of Electron‐Deficient Alkenes
154
Citations
57
References
2015
Year
Chemical EngineeringEngineeringPhotoredox ProcessPhotochemistryMechanistic PhotochemistryElectron-deficient AlkenesRadical (Chemistry)Synthetic PhotochemistryPhotocatalysisOrganic ChemistryElectron‐deficient AlkenesPhotoredox-catalyzed Reductive DifluoromethylationNeutral ConditionsChemistryHalogenation
Photoredox-catalyzed reductive difluoromethylation of electron-deficient alkenes was achieved in one step under tin-free, mild and neutral conditions. This protocol affords a facile method to introduce RCF2 (R=H, Ph, Me, and CH2N3) groups at sites β to electron-withdrawing groups. It was found that TTMS (tris(trimethylsilyl)silane) served nicely as both the H-atom donor and the electron donor in the catalytic cycle. Experimental and DFT computational results provided evidence that RCF2 (R=H, Ph, Me) radicals are nucleophilic in nature.
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