Direct Base-Assisted C‒H Cyclonickelation of 6-Phenyl-2,2′-bipyridine
| dc.contributor.author | Vogt, Nicolas | |
| dc.contributor.author | Sivchik, Vasily | |
| dc.contributor.author | Sandleben, Aaron | |
| dc.contributor.author | Hörner, Gerald | |
| dc.contributor.author | Klein, Axel | |
| dc.date.accessioned | 2020-04-29T14:28:00Z | |
| dc.date.available | 2020-04-29T14:28:00Z | |
| dc.date.issued | 2020-02-24 | |
| dc.date.updated | 2020-03-05T23:09:25Z | |
| dc.description.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. | en |
| dc.description.sponsorship | DFG, 53182490, EXC 314: Unifying Concepts in Catalysis | en |
| dc.description.sponsorship | DFG, 79971943, SFB 840: Von partikulären Nanosystemen zur Mesotechnologie | en |
| dc.identifier.eissn | 1420-3049 | |
| dc.identifier.uri | https://depositonce.tu-berlin.de/handle/11303/11046 | |
| dc.identifier.uri | http://dx.doi.org/10.14279/depositonce-9934 | |
| dc.language.iso | en | en |
| dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | en |
| dc.subject.ddc | 540 Chemie und zugeordnete Wissenschaften | de |
| dc.subject.other | cyclometalation | en |
| dc.subject.other | cyclonickelation | en |
| dc.subject.other | C–H activation | en |
| dc.subject.other | organonickel | en |
| dc.subject.other | base-assisted | en |
| dc.title | Direct Base-Assisted C‒H Cyclonickelation of 6-Phenyl-2,2′-bipyridine | en |
| dc.type | Article | en |
| dc.type.version | publishedVersion | en |
| dcterms.bibliographicCitation.articlenumber | 997 | en |
| dcterms.bibliographicCitation.doi | 10.3390/molecules25040997 | en |
| dcterms.bibliographicCitation.issue | 4 | en |
| dcterms.bibliographicCitation.journaltitle | Molecules | en |
| dcterms.bibliographicCitation.originalpublishername | MDPI | en |
| dcterms.bibliographicCitation.originalpublisherplace | Basel | en |
| dcterms.bibliographicCitation.volume | 25 | en |
| tub.accessrights.dnb | free | en |
| tub.affiliation | Fak. 2 Mathematik und Naturwissenschaften::Inst. Chemie | de |
| tub.affiliation.faculty | Fak. 2 Mathematik und Naturwissenschaften | de |
| tub.affiliation.institute | Inst. Chemie | de |
| tub.publisher.universityorinstitution | Technische Universität Berlin | en |