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Main Title: Direct Base-Assisted C‒H Cyclonickelation of 6-Phenyl-2,2′-bipyridine
Author(s): Vogt, Nicolas
Sivchik, Vasily
Sandleben, Aaron
Hörner, Gerald
Klein, Axel
Type: Article
Language Code: en
Abstract: 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.
Issue Date: 24-Feb-2020
Date Available: 29-Apr-2020
DDC Class: 540 Chemie und zugeordnete Wissenschaften
Subject(s): cyclometalation
C–H activation
Sponsor/Funder: DFG, 53182490, EXC 314: Unifying Concepts in Catalysis
DFG, 79971943, SFB 840: Von partikulären Nanosystemen zur Mesotechnologie
Journal Title: Molecules
Publisher: MDPI
Publisher Place: Basel
Volume: 25
Issue: 4
Article Number: 997
Publisher DOI: 10.3390/molecules25040997
EISSN: 1420-3049
Appears in Collections:Inst. Chemie » Publications

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