NHC/Phosphite Nickel(II) Precatalysts for the C-N Cross-Coupling of (Hetero)Aryl Chlorides under Mild Conditions
Nutan R Darandale1,2,3, Morgan E John4, Stephen A Moggach1
1School of Molecular Sciences, The University of Western Australia, Crawley, WA 6009, Australia.
Abstract:
We report the synthesis of three nickel complexes based on Ni(NHC)[P(OR)3](Ar)Cl and their application in C(sp2)-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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