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Photoredox/Ti Dual‐Catalyzed Dehydroxylation of Cyclobutanone Oximes for γ‐Cyanoalkyl Radical Generation: Access to Cyanoalkyl‐Substituted Oxoindolines
17
Citations
90
References
2022
Year
γ‐Cyanoalkyl Radical GenerationEngineeringSynthetic PhotochemistryOrganic ChemistryChemistryChemical EngineeringPhotoredox ProcessPhotocatalysisOrganometallic CatalysisCyclobutanone OximesPhotochemistryRadical (Chemistry)Diversity-oriented Synthesisγ‐Cyanoalkyl RadicalsCatalysisBiomolecular EngineeringCascade Radical Addition/cyclizationNatural SciencesPhotoredox/ti Dual‐catalyzed Dehydroxylation
Abstract In this work, we have established a photoredox/Ti dual‐catalyzed dehydroxylation of cyclobutanone oximes. The resulting γ‐cyanoalkyl radicals undergo a cascade radical addition/cyclization with N ‐acrylamides to afford cyanoalkyl substituted oxoindolines under mild conditions. This reaction also exhibits broad substrate scope and good functional group tolerance. Furthermore, it is applicable to late‐stage functionalization of complex molecules and gram‐scale synthesis, which illustrates its potential value in organic synthesis. magnified image
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