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

Mohammed Hashmat Ali; Bjorn Olesen; Brindaban Ranu; Luke Clippard; Jacqueline Heath; Garrett Meyer; Tawanika Williams

doi:10.1055/s-0035-1560834

Synthesis, Table of Contents

Synthesis 2016; 48(03): 429-436
DOI: 10.1055/s-0035-1560834

paper

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

Authors

Mohammed Hashmat Ali*

^aChemistry Department, Southeast Missouri State University, Cape Girardeau, Missouri 63701, USA Email: mhali@semo.edu
Bjorn Olesen

^aChemistry Department, Southeast Missouri State University, Cape Girardeau, Missouri 63701, USA Email: mhali@semo.edu
Brindaban Ranu

^bIndian Association for the Cultivation of Science, Jadavpur, Kolkata 700 032, India
Luke Clippard

^aChemistry Department, Southeast Missouri State University, Cape Girardeau, Missouri 63701, USA Email: mhali@semo.edu
Jacqueline Heath

^aChemistry Department, Southeast Missouri State University, Cape Girardeau, Missouri 63701, USA Email: mhali@semo.edu
Garrett Meyer

^aChemistry Department, Southeast Missouri State University, Cape Girardeau, Missouri 63701, USA Email: mhali@semo.edu
Tawanika Williams

^aChemistry Department, Southeast Missouri State University, Cape Girardeau, Missouri 63701, USA Email: mhali@semo.edu

Abstract

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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.

Key words

sulfides - sulfones - RuO₄ - dimethyl carbonate - green chemistry

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References

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Supplementary Material

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