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

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 Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2023, Volume: 72, Number: 9, Pages: 2095-2101 Pages count : 7 DOI: 10.1007/s11172-023-4004-x

Authors

Sigacheva V.L. ¹ , Kokorekin V.A. ^2,1 , Gorpinchenko N.V. ² , Lyalin B.V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
2	I. M. Sechenov First Moscow State Medical University of the Ministry of Health of the Russian Federation (Sechenov University), Moscow, Russian Federation

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%.

Sigacheva V.L. , Kokorekin V.A. , Gorpinchenko N.V. , Lyalin B.V.
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
Russian Chemical Bulletin. 2023. V.72. N9. P.2095-2101. DOI: 10.1007/s11172-023-4004-x WOS Scopus Scopus OpenAlex

≡ Web of science:	WOS:001074328300015
≡ Scopus:	2-s2.0-85172339308 \| 2-s2.0-85172879638
≡ OpenAlex:	W4387053739