Organic Letters · 2023 · 16 citations · 31 references
Natural SciencesChemistryCatalysisGreen ChemistryOrganic ChemistryCross-coupling ReactionsDiversity-oriented SynthesisHeterocycle SynthesisReaction MechanismsAryl Halide CouplingMild Reaction ConditionsNickel-catalyzed Cross-couplingPhotoredox CatalysisPhotoredox Cross-couplingPhotoredox FunctionalizationStereoselective Cross-couplingSubstrate Scope
An efficient photoredox/nickel dual-catalyzed coupling of allyl trifluoroborates with aryl halides has been developed, which provides an attractive route to diverse-substituted allylic benzenes. The method offers several advantages, such as high efficiency and regioselectivity, mild reaction conditions, wide substrate scope, and functional group compatibility. Mechanistic studies suggest that a π-allyl nickel(III) intermediate generated via the addition of an allyl radical to nickel species is possibly formed as a key reaction intermediate.
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Osvaldo Gutiérrez, John C. Tellis, David N. Primer et al. · Journal of the American Chemical Society · 2015 · 604 citations · Full text