NHC/Phosphite Nickel(II) Precatalysts for the C–N Cross-Coupling of (Hetero)Aryl Chlorides under Mild Conditions

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We report the synthesis of three nickel complexes based on Ni(NHC)[P(OR) 3 ](Ar)Cl and their application in C( sp 2 )–N cross-coupling reactions. Reactions involving secondary amines proceeded at room temperature, while anilines and primary alkyl amines coupled under mild heating. The reported complexes are air-stable as solids, operate at low catalytic loading, and do not require an exogenous ligand. Mechanistic studies suggest both free and Ni-bound phosphite are present during the reaction and that an isolated [Ni(NHC)(amine)(Ar)Cl] complex could be an on-cycle, catalytically active species.