Direct Base-Assisted C‒H Cyclonickelation of 6-Phenyl-2,2′-bipyridine
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. Dif...
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| Vydáno v: | Molecules (Basel, Switzerland) Ročník 25; číslo 4; s. 997 |
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24.02.2020
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| 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. |
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| AbstractList | 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. 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. 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.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. The organonickel complexes [Ni(Phbpy)X] (X = Br, OAc, CN) were obtained for the first time in a direct base-assisted arene C(sp )-H cyclometalation reaction from the rather unreactive precursor materials NiX and HPhbpy (6-phenyl-2,2'-bipyridine) or from the versatile precursor [Ni(HPhbpy)Br ] . 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. |
| Author | Hörner, Gerald Sandleben, Aaron Vogt, Nicolas Sivchik, Vasily Klein, Axel |
| AuthorAffiliation | 4 Institut für Chemie, Anorganische Chemie IV, Universität Bayreuth, Universitätsstraße 30, D-95440 Bayreuth, Germany; gerald.hoerner@uni-bayreuth.de 3 School of Chemistry, University of East Anglia, Earlham Road, Norwich NR4 7TJ, UK 1 Department für Chemie, Institut für Anorganische Chemie, Universität zu Köln, Greinstraße 6, D-50939 Köln, Germany 5 Theoretische Chemie, Technische Universität Berlin, Straße des 17. Juni 135, D-10623 Berlin, Germany 2 Department of Chemistry, University of Eastern Finland, 80101 Joensuu, Finland |
| AuthorAffiliation_xml | – name: 5 Theoretische Chemie, Technische Universität Berlin, Straße des 17. Juni 135, D-10623 Berlin, Germany – name: 4 Institut für Chemie, Anorganische Chemie IV, Universität Bayreuth, Universitätsstraße 30, D-95440 Bayreuth, Germany; gerald.hoerner@uni-bayreuth.de – name: 1 Department für Chemie, Institut für Anorganische Chemie, Universität zu Köln, Greinstraße 6, D-50939 Köln, Germany – name: 2 Department of Chemistry, University of Eastern Finland, 80101 Joensuu, Finland – name: 3 School of Chemistry, University of East Anglia, Earlham Road, Norwich NR4 7TJ, UK |
| Author_xml | – sequence: 1 givenname: Nicolas orcidid: 0000-0002-3437-4882 surname: Vogt fullname: Vogt, Nicolas – sequence: 2 givenname: Vasily orcidid: 0000-0003-3761-6661 surname: Sivchik fullname: Sivchik, Vasily – sequence: 3 givenname: Aaron orcidid: 0000-0002-4141-7406 surname: Sandleben fullname: Sandleben, Aaron – sequence: 4 givenname: Gerald orcidid: 0000-0002-3883-2879 surname: Hörner fullname: Hörner, Gerald – sequence: 5 givenname: Axel orcidid: 0000-0003-0093-9619 surname: Klein fullname: Klein, Axel |
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| Keywords | organonickel cyclometalation C–H activation base-assisted cyclonickelation |
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Am. Chem. Soc. doi: 10.1021/ja062856v |
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| Snippet | 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... The organonickel complexes [Ni(Phbpy)X] (X = Br, OAc, CN) were obtained for the first time in a direct base-assisted arene C(sp )-H cyclometalation reaction... 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... 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... |
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| SubjectTerms | base-assisted Catalysis Cations, Divalent Chemistry Techniques, Synthetic Coordination Complexes - chemical synthesis Cycloaddition Reaction cyclometalation cyclonickelation c–h activation Decomposition Experiments Humans Ligands Models, Chemical Nickel Nickel - chemistry organonickel Oxidation-Reduction Pyridines - chemistry Stereoisomerism |
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| Title | Direct Base-Assisted C‒H Cyclonickelation of 6-Phenyl-2,2′-bipyridine |
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