Intraligand Charge Transfer Enables Visible-Light-Mediated Nickel-Catalyzed Cross-Coupling Reactions.

Autor: Cavedon C; Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476, Potsdam, Germany.; Department of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195, Berlin, Germany., Gisbertz S; Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476, Potsdam, Germany.; Department of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195, Berlin, Germany., Reischauer S; Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476, Potsdam, Germany.; Department of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195, Berlin, Germany., Vogl S; Department of Chemistry, Functional Materials, Technische Universität Berlin, Hardenbergstraße 40, 10623, Berlin, Germany., Sperlich E; Institute of Chemistry, University of Potsdam, Karl-Liebknecht-Strasse 24-25, 14476, Potsdam, Germany., Burke JH; Department of Chemistry, University of Illinois Urbana-Champaign, Urbana, Illinois, 61801, USA., Wallick RF; Department of Chemistry, University of Illinois Urbana-Champaign, Urbana, Illinois, 61801, USA., Schrottke S; Department of Physics, Freie Universität Berlin, Arnimallee 22, 14195, Berlin, Germany., Hsu WH; Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476, Potsdam, Germany., Anghileri L; Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476, Potsdam, Germany.; Department of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195, Berlin, Germany., Pfeifer Y; Institute of Chemistry, University of Potsdam, Karl-Liebknecht-Strasse 24-25, 14476, Potsdam, Germany., Richter N; Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476, Potsdam, Germany., Teutloff C; Department of Physics, Freie Universität Berlin, Arnimallee 22, 14195, Berlin, Germany., Müller-Werkmeister H; Institute of Chemistry, University of Potsdam, Karl-Liebknecht-Strasse 24-25, 14476, Potsdam, Germany., Cambié D; Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476, Potsdam, Germany., Seeberger PH; Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476, Potsdam, Germany.; Department of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195, Berlin, Germany., Vura-Weis J; Department of Chemistry, University of Illinois Urbana-Champaign, Urbana, Illinois, 61801, USA., van der Veen RM; Department of Chemistry, University of Illinois Urbana-Champaign, Urbana, Illinois, 61801, USA.; Helmholtz Zentrum Berlin für Materialien und Energie GmbH, Hahn-Meitner-Platz 1, 14109, Berlin, Germany., Thomas A; Department of Chemistry, Functional Materials, Technische Universität Berlin, Hardenbergstraße 40, 10623, Berlin, Germany., Pieber B; Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476, Potsdam, Germany.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2022 Nov 14; Vol. 61 (46), pp. e202211433. Date of Electronic Publication: 2022 Oct 21.
DOI: 10.1002/anie.202211433
Abstrakt: We demonstrate that several visible-light-mediated carbon-heteroatom cross-coupling reactions can be carried out using a photoactive Ni II precatalyst that forms in situ from a nickel salt and a bipyridine ligand decorated with two carbazole groups (Ni(Czbpy)Cl 2 ). The activation of this precatalyst towards cross-coupling reactions follows a hitherto undisclosed mechanism that is different from previously reported light-responsive nickel complexes that undergo metal-to-ligand charge transfer. Theoretical and spectroscopic investigations revealed that irradiation of Ni(Czbpy)Cl 2 with visible light causes an initial intraligand charge transfer event that triggers productive catalysis. Ligand polymerization affords a porous, recyclable organic polymer for heterogeneous nickel catalysis of cross-coupling reactions. The heterogeneous catalyst shows stable performance in a packed-bed flow reactor during a week of continuous operation.
(© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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