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Open Access On the Ability of Nickel Complexes Derived from Tripodal Aminopyridine Ligands to Catalyze Arene Hydroxylations

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This article is Open Access under the terms of the Creative Commons CC BY-NC licence.

The development of catalysts for the selective hydroxylation of aromatic C–H bonds is an essential challenge in current chemical research. The accomplishment of this goal requires the discovery of powerful metal-based oxidizing species capable of hydroxylating inert aromatic bonds in a selective manner, avoiding the generation of non-selective oxygen-centered radicals. Herein we show an investigation on the ability of nickel(ii) complexes supported by tripodal tetradentate aminopyridine ligands to catalyze the direct hydroxylation of benzene to phenol with H2O2 as oxidant. We have found that modifications on the ligand structure of the nickel complex do not translate into different reactivity, which differs from previous findings for nickel-based arene hydroxylations. Besides, several nickel(ii) salts have been found to be effective in the oxidation of aromatic C–H bonds. The use of fluorinated alcohols as solvent has been found to result in an increase in phenol yield; however, showing no more than two turn-overs per nickel. These findings raise questions on the nature of the oxidizing species responsible for the arene hydroxylation reaction.
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Keywords: AROMATIC C–H OXIDATION; FLUORINATED SOLVENTS; HYDROGEN PEROXIDE; NICKEL COMPLEXES; PHENOLS

Document Type: Research Article

Affiliations: 1: Organic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG Utrecht, The Netherlands 2: Crystal and Structural Chemistry, Bijvoet Centre for Biomolecular Research, Utrecht University, Padualaan 8, 3584 CH Utrecht, The Netherlands 3: Organic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG Utrecht, The Netherlands;, Email: [email protected]

Publication date: June 1, 2020

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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