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

  • Cristian Cavedon
  • , Sebastian Gisbertz
  • , Susanne Reischauer
  • , Sarah Vogl
  • , Eric Sperlich
  • , John H. Burke
  • , Rachel F. Wallick
  • , Stefanie Schrottke
  • , Wei Hsin Hsu
  • , Lucia Anghileri
  • , Yannik Pfeifer
  • , Noah Richter
  • , Christian Teutloff
  • , Henrike Müller-Werkmeister
  • , Dario Cambié
  • , Peter H. Seeberger
  • , Josh Vura-Weis
  • , Renske M. van der Veen
  • , Arne Thomas
  • , Bartholomäus Pieber

Research output: Contribution to journalArticlepeer-review

Abstract

We demonstrate that several visible-light-mediated carbon−heteroatom cross-coupling reactions can be carried out using a photoactive NiII precatalyst that forms in situ from a nickel salt and a bipyridine ligand decorated with two carbazole groups (Ni(Czbpy)Cl2). 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)Cl2 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.

Original languageEnglish (US)
Article numbere202211433
JournalAngewandte Chemie - International Edition
Volume61
Issue number46
Early online dateOct 21 2022
DOIs
StatePublished - Nov 14 2022

Keywords

  • Flow Chemistry
  • Heterogeneous Catalysis
  • Homogeneous Catalysis
  • Nickel Catalysis
  • Photocatalysis

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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