Nickel-Catalyzed Chain-Walking Cross-Electrophile Coupling of Alkyl and Aryl Halides and Olefin Hydroarylation Enabled by Electrochemical Reduction

doi:10.1002/anie.201915418

. 2020 Apr 16;59(16):6513-6519.

doi: 10.1002/anie.201915418. Epub 2020 Mar 5.

Nickel-Catalyzed Chain-Walking Cross-Electrophile Coupling of Alkyl and Aryl Halides and Olefin Hydroarylation Enabled by Electrochemical Reduction

Gadde Sathish Kumar¹, Anatoly Peshkov¹, Aleksandra Brzozowska¹, Pavlo Nikolaienko¹, Chen Zhu¹, Magnus Rueping¹

Affiliations

PMID: 32017340
DOI: 10.1002/anie.201915418

Nickel-Catalyzed Chain-Walking Cross-Electrophile Coupling of Alkyl and Aryl Halides and Olefin Hydroarylation Enabled by Electrochemical Reduction

Gadde Sathish Kumar et al. Angew Chem Int Ed Engl. 2020.

. 2020 Apr 16;59(16):6513-6519.

doi: 10.1002/anie.201915418. Epub 2020 Mar 5.

Authors

Gadde Sathish Kumar¹, Anatoly Peshkov¹, Aleksandra Brzozowska¹, Pavlo Nikolaienko¹, Chen Zhu¹, Magnus Rueping¹

Affiliation

¹ KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900, Saudi Arabia.

PMID: 32017340
DOI: 10.1002/anie.201915418

Abstract

The first electrochemical approach for nickel-catalyzed cross-electrophile coupling was developed. This method provides a novel route to 1,1-diarylalkane derivatives from simple and readily available alkyl and aryl halides in good yields and excellent regioselectivity under mild conditions. The procedure shows good tolerance for a broad variety of functional groups and both primary and secondary alkyl halides can be used. Furthermore, the reaction was successfully scaled up to the multigram scale, thus indicating potential for industrial application. Mechanistic investigation suggested the formation of a nickel hydride in the electroreductive chain-walking arylation, which led to the development of a new nickel-catalyzed hydroarylation of styrenes to provide a series of 1,1-diaryl alkanes in good yields under mild reaction conditions.

Keywords: 1,1-diarylalkanes; electrosynthesis; migratory cross-coupling; nickel; β-hydride elimination.

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References

1. Reviews on reductive cross-electrophile coupling:
1. C. E. I. Knappke, S. Grupe, D. Gärtner, M. Corpet, C. Gosmini, A. Jacobi von Wangelin, Chem. Eur. J. 2014, 20, 6828;
1. T. Moragas, A. Correa, R. Martin, Chem. Eur. J. 2014, 20, 8242.
1. Reviews on transition-metal-catalyzed transformation of alkyl electrophiles:
1. A. Rudolph, M. Lautens, Angew. Chem. Int. Ed. 2009, 48, 2656;

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[1] Reviews on reductive cross-electrophile coupling:

[2] Reviews on reductive cross-electrophile coupling:

[3] C. E. I. Knappke, S. Grupe, D. Gärtner, M. Corpet, C. Gosmini, A. Jacobi von Wangelin, Chem. Eur. J. 2014, 20, 6828;

[4] C. E. I. Knappke, S. Grupe, D. Gärtner, M. Corpet, C. Gosmini, A. Jacobi von Wangelin, Chem. Eur. J. 2014, 20, 6828;

[5] T. Moragas, A. Correa, R. Martin, Chem. Eur. J. 2014, 20, 8242.

[6] T. Moragas, A. Correa, R. Martin, Chem. Eur. J. 2014, 20, 8242.

[7] Reviews on transition-metal-catalyzed transformation of alkyl electrophiles:

[8] Reviews on transition-metal-catalyzed transformation of alkyl electrophiles:

[9] A. Rudolph, M. Lautens, Angew. Chem. Int. Ed. 2009, 48, 2656;

[10] A. Rudolph, M. Lautens, Angew. Chem. Int. Ed. 2009, 48, 2656;

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Nickel-Catalyzed Chain-Walking Cross-Electrophile Coupling of Alkyl and Aryl Halides and Olefin Hydroarylation Enabled by Electrochemical Reduction

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Nickel-Catalyzed Chain-Walking Cross-Electrophile Coupling of Alkyl and Aryl Halides and Olefin Hydroarylation Enabled by Electrochemical Reduction

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