Issue 96, 2016

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

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

Supplementary files

Article information

Article type
Paper
Submitted
28 Jul 2016
Accepted
13 Sep 2016
First published
14 Sep 2016
This article is Open Access
Creative Commons BY license

RSC Adv., 2016,6, 93476-93485

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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