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

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

Journal

RSC Advances
ISSN: 2046-2069

Output data

Year: 2016, Volume: 6, Number: 96, Pages: 93476-93485 Pages count : 10 DOI: 10.1039/c6ra19190h

Authors

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

Affiliations

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

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.

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

Web of science:	WOS:000385631900034
Scopus:	2-s2.0-84991011179
OpenAlex:	W2520026702

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OpenAlex	35
Scopus	35
Web of science	35