Electrosynthesis of vinyl sulfones from alkenes and sulfonyl hydrazides mediated by KI: Аn electrochemical mechanistic study

Electrosynthesis of vinyl sulfones from alkenes and sulfonyl hydrazides mediated by KI: Аn electrochemical mechanistic study Full article

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 2017, Volume: 73, Number: 49, Pages: 6871-6879 Pages count : 9 DOI: 10.1016/j.tet.2017.10.047

Authors

Terent'ev Alexander O. ^1,2 , Mulina Olga M. ² , Pirgach Dmitry A. ^1,2 , Ilovaisky Alexey I. ² , Syroeshkin Mikhail A. ² , Kapustina Nadezhda I. ² , Nikishin Gennady I. ²

Affiliations

1	D.I. Mendeleev University of Chemical Technology of Russia, Moscow, 125047, Russian Federation
2	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 119991, Russian Federation

A variety of vinyl sulfones were prepared from alkenes and sulfonyl hydrazides via electrochemical oxidative sulfonylation. The reaction proceeds in an experimentally convenient undivided electrochemical cell equipped with graphite and iron electrodes employing KI as a redox catalyst and a supporting electrolyte. Applying extremely high current density up to 270 mA/cm2 permits rapid synthesis in a compact reactor and with small surface area electrodes. A possible reaction mechanism was proposed with the use of cyclic voltammetry. It is the combination of anodic and cathodic processes in this reaction that makes it possible to obtain products under mild conditions with yields from moderate to high.

Terent'ev A.O. , Mulina O.M. , Pirgach D.A. , Ilovaisky A.I. , Syroeshkin M.A. , Kapustina N.I. , Nikishin G.I.
Electrosynthesis of vinyl sulfones from alkenes and sulfonyl hydrazides mediated by KI: Аn electrochemical mechanistic study
Tetrahedron. 2017. V.73. N49. P.6871-6879. DOI: 10.1016/j.tet.2017.10.047 WOS Scopus OpenAlex

Web of science:	WOS:000416396000007
Scopus:	2-s2.0-85032576980
OpenAlex:	W2766175218

DB	Citing
OpenAlex	57
Scopus	55
Web of science	54