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Nickel‐Catalyzed Thermal Redox Functionalization of C(sp <sup>3</sup> )−H Bonds with Carbon Electrophiles**

Yuxin Gong, Lei Su, Zhaodong Zhu, Yang Ye, Hegui Gong

2022Angewandte Chemie International Edition44 citationsDOI

Abstract

Abstract C(sp 3 )−H bond coupling with carbon electrophiles remains rarely explored under thermo‐driven hydrogen atom transfer (HAT) conditions due to the challenge of integrating oxidation and reduction in a single operation. We report here a Ni‐catalyzed arylation and alkylation of C(sp 3 )−H bonds with organohalides to forge C(sp 3 )−C bonds by merging economical Zn and t BuOO t Bu (DTBP) as the external reductant and oxidant. The mild and easy‐to‐operate protocol enables facile carbofunctionalization of N‐/O‐α‐ and cyclohexane C−H bonds, and preparation of a few intermediates of bioactive compounds and drug derivatives. Preliminary mechanistic studies implied addition of an alkyl radical to a Ni II salt.

Topics & Concepts

ElectrophileCatalysisNickelSurface modificationRedoxChemistryCarbon fibersThermalOrganic chemistryMaterials sciencePhysical chemistryPhysicsComposite materialComposite numberMeteorologyCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsCatalytic Cross-Coupling Reactions
Nickel‐Catalyzed Thermal Redox Functionalization of C(sp <sup>3</sup> )−H Bonds with Carbon Electrophiles** | Litcius