The Journal of Organic Chemistry · 2021 · 26 citations · 51 references
Natural SciencesChemical EngineeringChemistryBiocatalysisCatalysisGreen ChemistryCatalyst DesignCatalytic MechanismsHeterocycle SynthesisMetal CatalysisPhotocatalysisPhotochemistryCatalyst IntegrationCopper CatalysisFunctional Group AnalysisFunctional Group ToleranceOxazole ChemistryOxazole SynthesisPhotocatalytic SynthesisPhotoredox Catalysis
Here, we report a mild and highly efficient approach to alkyl oxazoles through merging gold/copper catalysis and copper/photoredox catalysis. Various alkyl oxazoles are synthesized from N-propargylamides with alkyl halides in good to excellent yields with wide functional-group compatibility under blue-light irradiation. Significantly, a copper catalyst plays a dual role in this transformation: as a powerful cocatalyst to accelerate protodeauration of vinyl gold intermediates and improve photoredox catalysis.
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Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion
Xing‐Zhong Shu, Miao Zhang, Ying He et al. · Journal of the American Chemical Society · 2014 · 431 citations · Full text