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

The patterns of the reactions of anilines with NiO(OH), NaOCl, and NaOBr electro-generated in H 2 O and H 2 O—Bu t OH 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, NO 2 ) 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%.