Synthesis 2016; 48(03): 429-436
DOI: 10.1055/s-0035-1560834
paper
© Georg Thieme Verlag Stuttgart · New York

Oxidation of Aryl Sulfides to Sulfones with Alumina-Supported Ruthenium Catalyst in Dimethyl Carbonate–Water Media

Mohammed Hashmat Ali*
a   Chemistry Department, Southeast Missouri State University, Cape Girardeau, Missouri 63701, USA   eMail: mhali@semo.edu
,
Bjorn Olesen
a   Chemistry Department, Southeast Missouri State University, Cape Girardeau, Missouri 63701, USA   eMail: mhali@semo.edu
,
Brindaban Ranu
b   Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700 032, India
,
Luke Clippard
a   Chemistry Department, Southeast Missouri State University, Cape Girardeau, Missouri 63701, USA   eMail: mhali@semo.edu
,
Jacqueline Heath
a   Chemistry Department, Southeast Missouri State University, Cape Girardeau, Missouri 63701, USA   eMail: mhali@semo.edu
,
Garrett Meyer
a   Chemistry Department, Southeast Missouri State University, Cape Girardeau, Missouri 63701, USA   eMail: mhali@semo.edu
,
Tawanika Williams
a   Chemistry Department, Southeast Missouri State University, Cape Girardeau, Missouri 63701, USA   eMail: mhali@semo.edu
› Institutsangaben
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Publikationsverlauf

Received: 02. August 2015

Accepted after revision: 06. Oktober 2015

Publikationsdatum:
03. Dezember 2015 (online)


Abstract

A new procedure for the oxidation of sulfides to sulfones utilizing heterogeneous ruthenium reagent has been developed. A small amount of ruthenium trichloride (RuCl3) supported on alumina and excess sodium metaperiodate (NaIO4) was used to produce the ruthenium oxidizing catalyst in the reaction mixture. Sodium metaperiodate oxidized the pre-catalyst RuCl3 to RuO4 and also maintained a constant supply of RuO4 by oxidizing lower valent ruthenium ions during the course of the reaction. An environmentally friendly solvent mixture of dimethyl carbonate (DMC) and water was employed. A wide variety of aromatic sulfides were oxidized to sulfones in good to excellent yields by utilizing this procedure.

Supporting Information