Journal
ORGANOMETALLICS
Volume 24, Issue 25, Pages 6169-6178Publisher
AMER CHEMICAL SOC
DOI: 10.1021/om050224w
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The ligand precursor [LH2](2+.)2Br(-) (1) for the bis(NHC) ligand with N-picolyl moieties is synthesized in 83% yield. Complexation of 1 with palladium and nickel acetates produced [PdL](2+.)2Br(-) (2) and [NiL](2+.)2Br(-) (3), respectively, in quantitative yields. Metathesis reactions of 2 and 3 with AgPF6 give the corresponding bromide-free complexes [PdL](2+.)2PF(6)(-) (4) and [NiL](2+.)2PF(6)(-) (5). Complexes 2-4 were characterized by X-ray structural determinations, which reveal a highly twisted helical coordination of L around the metal ions. In solution, however, the tetradentate chelate ring undergoes a rapid fluxional process of ring twisting. A theoretical study confirms that the tetradentate coordination of L in 2 and 3 is energetically more favorable than the bidentate chelation mode with dangling picolyl groups. A preliminary application of [NiL](2+.)2Br(-) in Suzuki coupling of aryl halides with phenylboronic acid shows effective activity.
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