Copper(i)-mediated synthesis of β-hydroxysulfones from styrenes and sulfonylhydrazides: an electrochemical mechanistic study. Issue 96 (30th September 2016)

• Record Type: Journal Article
• Authors: Terent'ev, Alexander O.; Mulina, Olga M.; Pirgach, Dmitry A.; Demchuk, Dmitry V.; Syroeshkin, Mikhail A.; Nikishin, Gennady I.
• Is Part Of: RSC advances. Volume 6:Issue 96(2016)
• Page Start: 93476
• Page End: 93485
• Publication Date: 2016-09-30
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6ra19190h
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Copper(i ) halides were used as mediators in the synthesis of β-hydroxysulfones via the oxysulfonylation of styrenes using sulfonylhydrazides. 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.