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A new approach to the synthesis of azobenzenes based on the oxidative N—N coupling of anilines under the action of electrogenerated NiO(OH), NaOCl, and NaOBr

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Abstract

The patterns of the reactions of anilines with NiO(OH), NaOCl, and NaOBr electro-generated in H2O and H2O—ButOH have been studied for the first time. It was found that NiO(OH) is efficient with respect to anilines with one donor (Me, OMe) or one weak acceptor (Cl, Br) substituent in the benzene ring, while NaOCl and NaOBr are more active towards anilines with one strong acceptor (CN, NO2) or several weak acceptor (Cl) substituents. Based on the results obtained, an approach has been proposed to the two-stage synthesis of a number of azobenzenes under mild conditions with a yield of up to 48%.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. L. Sigacheva, V. A. Kokorekin & B. V. Lyalin

  2. I. M. Sechenov First Moscow State Medical University of the Ministry of Health of the Russian Federation (Sechenov University), Build. 2, 8 ul. Trubetskaya, 119991, Moscow, Russian Federation

    V. A. Kokorekin & N. V. Gorpinchenko

Authors
  1. V. L. Sigacheva
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  2. V. A. Kokorekin
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  3. N. V. Gorpinchenko
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  4. B. V. Lyalin
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Corresponding author

Correspondence to B. V. Lyalin.

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The authors declare no competing interests.

Additional information

This work was performed under financial support of the Russian Foundation for Basic Research (Project No. 19-29-08027).

No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 9, pp. 2095–2101, September, 2023.

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Sigacheva, V.L., Kokorekin, V.A., Gorpinchenko, N.V. et al. A new approach to the synthesis of azobenzenes based on the oxidative N—N coupling of anilines under the action of electrogenerated NiO(OH), NaOCl, and NaOBr. Russ Chem Bull 72, 2095–2101 (2023). https://doi.org/10.1007/s11172-023-4004-x

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  • DOI: https://doi.org/10.1007/s11172-023-4004-x

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