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Copper(I)‐Catalyzed Decarboxylative <i>N</i>‐Phosphorylation: Modular Preparation of <i>N</i>‐Acyl Iminophosphoranes Using Dioxazolones and Phosphines

Jin-Hwan Park, Anattil Unnikrishnan Krishnapriya, Yeongmi Park, Minsuk Kim, Tyler W. Reidl, Rositha Kuniyil, Jongwoo Son

2023Advanced Synthesis & Catalysis10 citationsDOIOpen Access PDF

Abstract

Abstract Dioxazolones and phosphines have been used to access N ‐acyl iminophosphoranes in copper(I) catalysis under simple thermal conditions. The synthetic utility of this protocol is demonstrated by a broad range of substrates with an excellent atom‐economy. The optimization process showed that copper demonstrated as catalytic amount toward the targeted transformation. Functionalization studies of N ‐acyl iminophosphoranes were also conducted. Our reaction protocol is compatible with an example of a bioactive motif‐containing N ‐acyl iminophosphorane analogue.

Topics & Concepts

ChemistryCatalysisCopperCombinatorial chemistrySurface modificationOrganic chemistryPhysical chemistryCatalytic C–H Functionalization MethodsChemical Synthesis and AnalysisSynthesis and Catalytic Reactions
Copper(I)‐Catalyzed Decarboxylative <i>N</i>‐Phosphorylation: Modular Preparation of <i>N</i>‐Acyl Iminophosphoranes Using Dioxazolones and Phosphines | Litcius