A Chemoselective Oxidation of Sulfides to Sulfoxides and Sulfones Using Urea-2,2-dihydroperoxypropane as a Novel Oxidant

Author(s): Kaveh Khosravi, Shirin Naserifar, Atefeh Asgari.

Journal Name: Letters in Organic Chemistry

Volume 13 , Issue 10 , 2016

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Graphical Abstract:


Background: Sulfoxides and sulfones have been in the center of attention due to their wide range of promises in various approaches. The functional groups presented in these compounds serve as important building blocks in numerous natural, pharmeceutical and agricultural compounds. These deriatives have been prepared through a multitude of routes which were accompanied by several drawbacks. Therefore, there has been an ever-increasing interest to find a new methodology that leads to the production of these compounds via an environmentally benign path bringing about high yields. Recently, gem-dihydroperoxides have attracted much attention due to their oxidizing power and they have been utilized in several oxidation processes.

Methods: We carried out a chemoselective oxidation of sulfides to sulfoxides and sulfones on treatment with urea-2,2-dihydroperoxypropane, a solid oxidant composed of equal amounts of 2,2- dihydroperoxypropane and urea, using THF as the solvent under catalyst-free conditions at room temperature.

Results: Sulfides possessing a variety of substitutions namely dialkyl, diaryl, ally l and alkyl-aryl were subjected to the optimized reaction conditions and they could successfully afford different amounts of sulfoxides and sulfones depending on the amount of the oxidant utilized. Based on the results, electrondonating groups accelerated the reaction while electron-withdrawing substituents lowered the reactivity.

Conclusion: Urea-2,2-dihydroperoxypropane as a solid oxidant which can be stored for several months without any loss in its activity has proved its capability to oxidize sulfides to sulfoxides and sulfones under catalyst-free and mild conditions. This approach is a cost-effective and environmentally benign methodology via which the products have been synthesized in high yields and short reaction times.

Keywords: Chemoselective oxidation, sulfides, sulfoxides, sulfones, Urea-2, 2dihydroperoxypropane.

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Article Details

Year: 2016
Page: [749 - 756]
Pages: 8
DOI: 10.2174/1570178614666161123115100
Price: $65

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