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Issue 96, 2016
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Copper(i)-mediated synthesis of β-hydroxysulfones from styrenes and sulfonylhydrazides: an electrochemical mechanistic study

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Abstract

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.

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

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Supplementary files

Article information


Submitted
28 Jul 2016
Accepted
13 Sep 2016
First published
14 Sep 2016

This article is Open Access

RSC Adv., 2016,6, 93476-93485
Article type
Paper

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

A. O. Terent'ev, O. M. Mulina, D. A. Pirgach, D. V. Demchuk, M. A. Syroeshkin and G. I. Nikishin, RSC Adv., 2016, 6, 93476
DOI: 10.1039/C6RA19190H

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