Direct base-assisted C‒H cyclonickelation of 6-phenyl-2,2'-bipyridine

Vogt, Nicolas, Sivchik, Vasily, Sandleben, Aaron, Hörner, Gerald and Klein, Axel (2020) Direct base-assisted C‒H cyclonickelation of 6-phenyl-2,2'-bipyridine. Molecules, 25 (4). ISSN 1420-3049

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The organonickel complexes [Ni(Phbpy)X] (X = Br, OAc, CN) were obtained for the first time in a direct base-assisted arene C(sp2)-H cyclometalation reaction from the rather unreactive precursor materials NiX2 and HPhbpy (6-phenyl-2,2'-bipyridine) or from the versatile precursor [Ni(HPhbpy)Br2]2. Different from previously necessary C‒Br oxidative addition at Ni(0), an extended scan of reaction conditions allowed quantitative access to the title compound from Ni(II) on synthetically useful timescales through base-assisted C‒H activation in nonpolar media at elevated temperature. Optimisation of the reaction conditions (various bases, solvents, methods) identified 1:2 mixtures of acetate and carbonate as unrivalled synergetic base pairs in the optimum protocol that holds promise as a readily usable and easily tuneable access to a wide range of direct nickelation products. While for the base-assisted C‒H metalation of the noble metals Ru, Ir, Rh, or Pd, this acetate/carbonate method has been established for a few years, our study represents the leap into the world of the base metals of the 3d series.

Item Type: Article
Uncontrolled Keywords: 6-phenyl-2,2-bipyridine,activation,bonds,c-h activation,crystal-structure,functionalization,ligand,nickel(ii) complexes,palladium(ii),platinum,pt-ii,base-assisted,cyclometalation,cyclonickelation,organonickel
Faculty \ School: Faculty of Science > School of Chemistry
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Depositing User: LivePure Connector
Date Deposited: 03 Mar 2020 09:10
Last Modified: 22 Oct 2022 05:55
DOI: 10.3390/molecules25040997


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