Electrochemically induced oxidative S–O coupling: synthesis of sulfonates from sulfonyl hydrazides and N-hydroxyimides or N-hydroxybenzotriazoles

Electrochemically induced oxidative S–O coupling: synthesis of sulfonates from sulfonyl hydrazides and N-hydroxyimides or N-hydroxybenzotriazoles Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2019, Volume: 17, Number: 14, Pages: 3482-3488 Pages count : 7 DOI: 10.1039/c8ob03162b

Authors

Terent'ev Alexander O. ^1,2 , Mulina Olga M. ¹ , Parshin Vadim D. ² , Kokorekin Vladimir A. ^1,3 , Nikishin Gennady I. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, Moscow, Russian Federation
2	D.I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya square, Moscow, Russian Federation
3	Sechenov First Moscow State Medical University, 8-2 Trubetskaya St., Moscow, Russian Federation

The process of oxidative S–O coupling under the action of electric current was developed. Aryl, hetaryl and alkyl sulfonyl hydrazides and N-hydroxy compounds (N-hydroxyimides and N-hydroxybenzotriazoles) are applied as starting reagents for the preparation of sulfonates. The reaction is carried out under constant current conditions in an experimentally convenient undivided electrochemical cell equipped with a graphite anode and a stainless steel cathode under a high current density (60 mA cm−2). NH4Br in this process acts as a supporting electrolyte and participates in the oxidation of the starting compounds to form a coupling product. The developed strategy represents a quite atom-efficient approach: one partner loses two nitrogen and three hydrogen atoms, while another one loses only one hydrogen atom. Cyclic voltammetry and the control experiment allowed us to propose possible reaction pathways: generated through anodic oxidation molecular bromine or its higher oxidation state derivatives oxidize the starting compounds to form reactive species, which couple to form the S–O bond.

Terent'ev A.O. , Mulina O.M. , Parshin V.D. , Kokorekin V.A. , Nikishin G.I.
Electrochemically induced oxidative S–O coupling: synthesis of sulfonates from sulfonyl hydrazides and N-hydroxyimides or N-hydroxybenzotriazoles
Organic & Biomolecular Chemistry. 2019. V.17. N14. P.3482-3488. DOI: 10.1039/c8ob03162b WOS Scopus OpenAlex

≡ Web of science:	WOS:000465615200021
≡ Scopus:	2-s2.0-85064056222
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