Universität zu Köln

Vogt, Nicolas ORCID: 0000-0002-3437-4882, Sivchik, Vasily ORCID: 0000-0003-3761-6661, Sandleben, Aaron ORCID: 0000-0002-4141-7406, Hoerner, Gerald ORCID: 0000-0002-3883-2879 and Klein, Axel ORCID: 0000-0003-0093-9619 (2020). Direct Base-Assisted C-H Cyclonickelation of 6-Phenyl-2,2 '-bipyridine. Molecules, 25 (4). BASEL: MDPI. ISSN 1420-3049

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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(sp(2))-H cyclometalation reaction from the rather unreactive precursor materials NiX2 and HPhbpy (6-phenyl-2,2'-bipyridine) or from the versatile precursor [Ni(HPhbpy)Br-2](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:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Vogt, Nicolas UNSPECIFIED orcid.org/0000-0002-3437-4882 UNSPECIFIED Sivchik, Vasily UNSPECIFIED orcid.org/0000-0003-3761-6661 UNSPECIFIED Sandleben, Aaron UNSPECIFIED orcid.org/0000-0002-4141-7406 UNSPECIFIED Hoerner, Gerald UNSPECIFIED orcid.org/0000-0002-3883-2879 UNSPECIFIED Klein, Axel UNSPECIFIED orcid.org/0000-0003-0093-9619 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-345716
DOI:	10.3390/molecules25040997
Journal or Publication Title:	Molecules
Volume:	25
Number:	4
Date:	2020
Publisher:	MDPI
Place of Publication:	BASEL
ISSN:	1420-3049
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Inorganic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language NICKEL(II) COMPLEXES; CRYSTAL-STRUCTURE; PT-II; PLATINUM; BONDS; 6-PHENYL-2,2-BIPYRIDINE; FUNCTIONALIZATION; PALLADIUM(II); ACTIVATION; LIGAND Multiple languages Biochemistry & Molecular Biology; Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/34571