Ruthenium Phenoxo Complexes: An Isolobal Ligand to Cp with Improved Properties

Schulte, Tim; Wang, Zikuan; Li, Chen-Chen; Hamad, Aboubakr; Waldbach, Felix; Pampel, Julius; Petzold, Roland; Leutzsch, Markus; Bahns, Fritz; Ritter, Tobias

doi:10.1021/jacs.4c02088

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Ruthenium Phenoxo Complexes: An Isolobal Ligand to Cp with Improved Properties

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Schulte, Tim
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Institute of Organic Chemistry, RWTH Aachen University;

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Wang, Zikuan
Research Group Manganas, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons298980

Li, Chen-Chen
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons243562

Hamad, Aboubakr
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Institute of Organic Chemistry, RWTH Aachen University;

/persons/resource/persons298077

Waldbach, Felix
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons298982

Pampel, Julius
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons243564

Petzold, Roland
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons132873

Leutzsch, Markus
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

Bahns, Fritz
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Institute of Organic Chemistry, RWTH Aachen University;

/persons/resource/persons198096

Ritter, Tobias
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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引用

Schulte, T., Wang, Z., Li, C.-C., Hamad, A., Waldbach, F., Pampel, J., Petzold, R., Leutzsch, M., Bahns, F., & Ritter, T. (2024). Ruthenium Phenoxo Complexes: An Isolobal Ligand to Cp with Improved Properties. Journal of the American Chemical Society, 146(23), 15825-15832. doi:10.1021/jacs.4c02088.

引用: https://hdl.handle.net/21.11116/0000-000F-6CBF-2

要旨

Catalytic π-arene activation is based on catalysts that allow for arene exchange. To date, cyclopentadiene (Cp)-derived catalysts are the most commonly used in π-arene activation despite their low arene exchange rates. Herein, we report the synthesis, analysis, and catalytic application of Ru(II) complexes supported by phenoxo ligands, which are isolobal alternatives to Cp. The phenoxo complexes exhibit arene exchange rates significantly faster than those of the corresponding Cp complexes. The rate can be further increased through the choice of appropriate counterions. The mechanism of the arene exchange process is elucidated by kinetic and computational analyses. We demonstrate the utility of the new catalysts through an S_NAr reaction between fluorobenzene and alcohols, including secondary alcohols that could not be used previously in related reactions. Moreover, the catalytic thermal decarboxylation of phenylacetic acids is presented.