Publication | Closed Access
Generation of Alkoxyl Radicals by Photoredox Catalysis Enables Selective C(sp<sup>3</sup>)−H Functionalization under Mild Reaction Conditions
90
Citations
50
References
2015
Year
EngineeringOrganic ChemistryChemistryMild Reaction ConditionsChemical EngineeringPhotoredox ProcessPhotocatalysisAlkoxyl RadicalsSp 3DerivativesPhotochemistryMechanistic PhotochemistryRadical (Chemistry)Diversity-oriented SynthesisHantzsch EsterCatalysisBiomolecular EngineeringFunctionalization ReactionNatural Sciences
Abstract Reported herein is the first visible‐light‐induced formation of alkoxyl radicals from N‐alkoxyphthalimides, and the Hantzsch ester as the reductant is crucial for the reaction. The selective hydrogen atom abstraction by the alkoxyl radical enables C(sp 3 )−H allylation and alkenylation reactions under mild reaction conditions at room temperature. Broad substrate variations, including a structurally complexed steroid, undergo the C(sp 3 )−H functionalization reaction effectively with high regio‐ and chemoselectivity.
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