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Nickel-Catalyzed Reductive 2-Pyridination of Aryl Iodides with Difluoromethyl 2-Pyridyl Sulfone

Wenjun Miao, Chuanfa Ni, Pan Xiao, Rulong Jia, Wei Zhang, Jinbo Hu

2021Organic Letters43 citationsDOI

Abstract

A novel nickel-catalyzed reductive cross-coupling between aryl iodides and difluoromethyl 2-pyridyl sulfone (2-PySO2CF2H) enables C(sp2)–C(sp2) bond formation through selective C(sp2)–S bond cleavage, which demonstrates the new reactivity of 2-PySO2CF2H reagent. This method employs readily available nickel catalyst and sulfones as cross-electrophile coupling partners, providing facile access to biaryls under mild reaction conditions without pregeneration of arylmetal reagents.

Topics & Concepts

ChemistryReagentArylNickelCatalysisSulfoneElectrophileReactivity (psychology)Reductive eliminationCombinatorial chemistryBond cleavageCoupling reactionMedicinal chemistryOrganic chemistryAlkylAlternative medicinePathologyMedicineSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions
Nickel-Catalyzed Reductive 2-Pyridination of Aryl Iodides with Difluoromethyl 2-Pyridyl Sulfone | Litcius