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Electrochemically induced oxidative S–O coupling: synthesis of sulfonates from sulfonyl hydrazides and N-hydroxyimides or N-hydroxybenzotriazolesстатья
Статья опубликована в высокорейтинговом журнале
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 21 мая 2019 г.
- Авторы: Terent’ev A.O., Mulina O.M., Parshin V.D., Kokorekin V.A., Nikishin G.I.
- Журнал: Organic and Biomolecular Chemistry
- Том: 17
- Номер: 14
- Год издания: 2019
- Издательство: Royal Society of Chemistry
- Местоположение издательства: United Kingdom
- Первая страница: 3482
- Последняя страница: 3488
- DOI: 10.1039/c8ob03162b
- Аннотация: 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.
- Добавил в систему: Мулина Ольга Михайловна