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Copper(i)-mediated synthesis of β-hydroxysulfones from styrenes and sulfonylhydrazides: an electrochemical mechanistic study Научная публикация

Журнал RSC Advances
ISSN: 2046-2069
Вых. Данные Год: 2016, Том: 6, Номер: 96, Страницы: 93476-93485 Страниц : 10 DOI: 10.1039/c6ra19190h
Авторы Terent'ev Alexander O. 1,2 , Mulina Olga M. 1 , Pirgach Dmitry A. 1,2 , Demchuk Dmitry V. 1 , Syroeshkin Mikhail A. 1 , Nikishin Gennady I. 1
Организации
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow, Russian Federation
2 D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya square, Moscow, Russian Federation

Реферат: Copper(I) halides were used as mediators in the synthesis of β-hydroxysulfones via the oxysulfonylation of styrenes using sulfonylhydrazides. The feature of the developed process lies in the combination of a copper(I) salt with oxygen—the stoichiometric oxidant. Copper(II) species are responsible for the oxidation of sulfonylhydrazides, they are generated in small amounts in the O2/Cu(I)/Cu(II) redox system, which is formed during the reaction. The combination of these three components enables one to obtain in the case of α-methylstyrenes only β-hydroxysulfones and in the case of α-unsubstituted styrenes, β-hydroxysulfones as the main products and β-ketosulfones as the by-products. With good yields β-hydroxysulfones were prepared by reduction of the reaction mixture containing both products β-hydroxysulfones and β-ketosulfones with NaBH4. An electrochemical study revealed that the Cu(I)/Cu(II) pair can serve as an effective mediator of β-hydroxysulfones formation via redox processes.
Библиографическая ссылка: Terent'ev A.O. , Mulina O.M. , Pirgach D.A. , Demchuk D.V. , Syroeshkin M.A. , Nikishin G.I.
Copper(i)-mediated synthesis of β-hydroxysulfones from styrenes and sulfonylhydrazides: an electrochemical mechanistic study
RSC Advances. 2016. V.6. N96. P.93476-93485. DOI: 10.1039/c6ra19190h WOS Scopus OpenAlex
Идентификаторы БД:
Web of science: WOS:000385631900034
Scopus: 2-s2.0-84991011179
OpenAlex: W2520026702
Цитирование в БД:
БД Цитирований
OpenAlex 35
Scopus 35
Web of science 35
Альметрики: