Electrooxidative Thiocyanation of Hydroxy‐ and Alkoxybenzenes

Electrooxidative Thiocyanation of Hydroxy‐ and Alkoxybenzenes Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2024, Volume: 27, Number: 47, Article number : e202400937, Pages count : DOI: 10.1002/ejoc.202400937

Authors

Moiseeva Nataliya V. ¹ , Sokolov Alexey ¹ , Andreev Ivan ¹ , Ratmanova Nina ¹ , Trushkov Igor ¹ , Kokorekin Vladimir ^1,2

Affiliations

1	FSBIS N D Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences NA RUSSIAN FEDERATION
2	Sechenov First Moscow State Medical University, Trubetskaya st. 8–2, Moscow, 119991 Russian Federation

We developed an original method for thiocyanation of hydroxy- and alkoxy-substituted benzenes (including naturally occurring compounds) using electrogenerated thiocyanogen, (SCN)₂. The presence of zinc chloride as a Lewis acid significantly enhances reaction efficiency by activating thiocyanogen. Cyclic voltammetry of the reactants and their combinations was employed to optimize reaction conditions and investigate the proposed mechanisms. This method demonstrated broad synthetic utility, leading to mono- and bis-thiocyanated arenes and various heterocycles with yields 36–97 %. Notable products include the neuroprotective drug riluzole and precursors for the antiprotozoal drugs toltrazuril and ponazuril.

Moiseeva N.V. , Sokolov A. , Andreev I. , Ratmanova N. , Trushkov I. , Kokorekin V.
Electrooxidative Thiocyanation of Hydroxy‐ and Alkoxybenzenes
European Journal of Organic Chemistry. 2024. V.27. N47. e202400937 . DOI: 10.1002/ejoc.202400937 WOS OpenAlex

Web of science:	WOS:001344756900001
OpenAlex:	W4402382930

Пока нет цитирований