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Nickel-Catalyzed Cyanation of Aryl Thioethers

Tristan Delcaillau, Adrian Woenckhaus-Alvarez, Bill Morandi

2021Organic Letters48 citationsDOIOpen Access PDF

Abstract

as a cyanide source has been developed to access functionalized aryl nitriles. The ligand dcype (1,2-bis(dicyclohexylphosphino)ethane) in combination with the base KOAc (potassium acetate) is essential for achieving this transformation efficiently. This reaction involves both a C-S bond activation and a C-C bond formation. The scalability, low catalyst and reagents loadings, and high functional group tolerance have enabled both late-stage derivatization and polymer recycling, demonstrating the reaction's utility across organic chemistry.

Topics & Concepts

CyanationChemistryArylCatalysisReagentCyanideNickelCombinatorial chemistryLigand (biochemistry)DerivatizationPotassium cyanideOrganic chemistryMedicinal chemistryBiochemistryAlkylHigh-performance liquid chromatographyReceptorSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions