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Article Abstract

We report the synthesis of three nickel complexes based on Ni(NHC)[P(OR)](Ar)Cl and their application in C()-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.

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http://dx.doi.org/10.1021/acs.orglett.5c03230DOI Listing

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We report the synthesis of three nickel complexes based on Ni(NHC)[P(OR)](Ar)Cl and their application in C()-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.

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