Photoredox/Nickel Dual-Catalyzed Reductive Cross Coupling of Aryl Halides Using an Organic Reducing Agent

Embargo End Date
2021-02-03

Type
Article

Authors
Dewanji, Abhishek
Bülow, Raoul F.
Rueping, Magnus

KAUST Department
Chemical Science Program
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division

Online Publication Date
2020-02-03

Print Publication Date
2020-02-21

Date
2020-02-03

Submitted Date
2020-01-14

Abstract
A successful protocol for the reductive aryl−aryl cross-coupling of polyfluorinated arenes with a broad range of aryl halides has been developed. Sequential carbon−fluorine bond cleavage and carbon−carbon bond formation are two of the important features of the reaction. Addition of an aryl radical anion to a nickel intermediate was achieved for the first time using polyfluoroarenes as radical precursors. This, in combination with the excellent para selectivity, paves the way for the synthesis of various new multifluorinated biaryl compounds.

Citation
Dewanji, A., Bülow, R. F., & Rueping, M. (2020). Photoredox/Nickel Dual-Catalyzed Reductive Cross Coupling of Aryl Halides Using an Organic Reducing Agent. Organic Letters. doi:10.1021/acs.orglett.0c00199

Acknowledgements
The research leading to these results has received funding from the European Research Council under the European Union’s Seventh Framework Programme (FP/2007−2013)/ERC Grant Agreement No. 617044 (SunCatChem).
We thank Frau Cornelia Vermeeren for carrying out purifications by preparative HPLC.

Publisher
American Chemical Society (ACS)

Journal
Organic Letters

DOI
10.1021/acs.orglett.0c00199

Additional Links
https://pubs.acs.org/doi/10.1021/acs.orglett.0c00199

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