Synthesis and catalytic application of cyclopentadienyl nickel(II) N-heterocyclic carbene complexes
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A series of ester-functionalized benzimidazolium salts2a-cwere prepared by quaternization of 1-{(ethoxycarbonyl)methyl}benzimidazole (1) with 3,5-dimethylbenzyl bromide, 2,5-dimethylbenzyl chloride and 3-methoxybenzyl chloride, respectively. Refluxing2a-cwith nickelocene in THF yielded the neutral cyclopentadienyl NHC nickel(II) complexes3a-c. Their structures were defined by NMR, IR and elemental analysis techniques. Molecular weights of3a-cwere affirmed by MALDI-TOF mass spectrometry. Catalytic tests of3a-cwere performed in Kumada coupling of some aryl chlorides with phenylmagnesium bromide at 25 degrees C. [GRAPHICS] .
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GRIGNARD-REAGENTS , BOND FORMATION , ARYL , LIGANDS , HALIDES , HYDROSILYLATION , HETEROARYL , PALLADIUM , ARYLATION , CHLORIDES