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  • Title: Nickel(II) complexes of bidentate N-heterocyclic carbene/phosphine ligands: efficient catalysts for Suzuki coupling of aryl chlorides.
    Author: Lee CC, Ke WC, Chan KT, Lai CL, Hu CH, Lee HM.
    Journal: Chemistry; 2007; 13(2):582-91. PubMed ID: 16969780.
    Abstract:
    Nickel(II) complexes of bidentate N-heterocyclic carbene (NHC)/phosphane ligand L were prepared and structurally characterized. Unlike palladium, which forms [PdCl(2)(L)], the stable nickel product isolated is the ionic [Ni(L)(2)]Cl(2). These Ni(II) complexes are highly robust in air. Among different N-substituents on the ligand framework, the nickel complex of ligand L bearing N-1-naphthylmethyl groups (2 a) is a highly effective catalyst for Suzuki cross-coupling between phenylboronic acid and a range of aryl halides, including unreactive aryl chlorides. The activities of 2 a are largely superior to those of other reported nickel NHC complexes and their palladium counterparts. Unlike the previously reported [NiCl(2)(dppe)] (dppe=1,2-bis(diphenylphosphino)ethane), 2 a can effectively catalyze the cross-coupling reaction without the need for a catalytic amount of PPh(3), and this suggests that the PPh(2) functionality of hybrid NHC ligand L can partially take on the role of free PPh(3). However, for unreactive aryl chlorides at low catalyst loading, the presence of PPh(3) accelerates the reaction.
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