Organic Letters · 2023 · 15 citations · 43 references
Natural SciencesChemistryCatalysisGreen ChemistryOrganic ChemistryCatalytic MechanismsElimination ReactionsOrganic SynthesisPhotocatalysisPhotochemical SynthesisPhotochemistryChemoselective FunctionalizationChemoselective SynthesisElimination From Alkyl HalidesHydrogen Atom TransferLigand FunctionalizationPalladium CatalystsRegioselectivitySide Reactions
Presented is a highly efficient method for visible-light-induced regio- and chemoselective elimination of alkyl halides yielding unactivated terminal olefins vital in organic synthesis. Achieved through ligand control, the reaction exhibits remarkable regioselectivity and suppresses undesired side reactions, particularly 1,5-hydrogen atom transfer (HAT). The process favors primary alkyl halides while preserving secondary and tertiary alkyl bromides, thereby enabling the incorporation of terminal olefins in complex molecules for late-stage functionalization.
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