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Journal Article

Intraligand charge transfer enables visible-light-mediated nickel-catalyzed cross-coupling reactions

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Cavedon,  Cristian
Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Gisbertz,  Sebastian
Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Reischauer,  Susanne
Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Hsu,  Wei-hsin
Dario Cambié, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Anghileri,  Lucia
Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

Richter, Noah,  Noah
Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Cambié,  Dario       
Dario Cambié, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.       
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Pieber,  Bartholomäus       
Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Cavedon, C., Gisbertz, S., Reischauer, S., Vogl, S., Sperlich, E., Burke, J. H., et al. (2022). Intraligand charge transfer enables visible-light-mediated nickel-catalyzed cross-coupling reactions. Angewandte Chemie International Edition, 61(46): e202211433. doi:10.1002/anie.202211433.


Cite as: https://hdl.handle.net/21.11116/0000-000B-65B7-5
Abstract
We demonstrate that several visible-light mediated carbon–heteroatom cross-couplings 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-couplings follows a hitherto undisclosed mechanism that is different from previously reported light-responsive nickel complexes that were reported to undergo metal-to-ligand charge transfer. Theoretic 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-couplings. The heterogeneous catalyst shows stable performance in a packed-bed flow reactor during a week of continuous operation.