The Journal of Organic Chemistry · 2023 · 17 citations · 39 references
Natural SciencesChemistryCatalysisOrganic ChemistryCatalytic MaterialsCross-coupling ReactionsPhotocatalysisPhotochemical SynthesisPhotochemistryRadical ReactionsCopper-catalyzed CouplingCopper-catalyzed OxidationFunctionalizationPhotoactive Metal ComplexesPhotochemical FunctionalizationStereoselective C-h FunctionalizationTransition Metal-catalyzed SynthesisTransition-metal-catalyzed Functionalization
Described herein is a photoinduced copper-catalyzed 1,2-difunctionalization of 1,3-dienes. The selenium atom radical was generated by the visible light irradiation of diselenides, triggering radical addition with 1,3-dienes to form allyl radical intermediate. Subsequent rapid Z / E isomerization allowed for thermodynamically favorable intermediate formation and enabled copper catalyzed stereoselective functionalization with various nucleophiles.
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Recent progress in selenium-catalyzed organic reactions
Li‐Xiong Shao, Yiming Li, Jian‐Mei Lu et al. · Organic Chemistry Frontiers · 2019 · 226 citations