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Procedure for the aerobic oxidation of a sulfoxide group to a sulfone

OTRI

ubu

Procedure for the aerobic oxidation of a sulfoxide group to a sulfone.

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Description

The present invention relates to a procedure for the oxidation of a sulfoxide group to a sulfone group. The procedure consists in the oxidation of the sulfoxide with air in the presence of a molibdenum compound as catalyst, preferentially dioxomolibdenum (VI) bis(acetilacetonate) or dinuclear derivatives coming from its partial hydrolisis.

Innovative aspects

The main novelty of the present method is the use of air as oxidating agent, while clasical procedures make use of hydrogen peroxide, risky to store and handle due to its corrosive nature and explosive vapors.

Specifications

The present invention relates to a procedure for the oxidation of sulfoxides to sulfones using the oxygen from the air as oxidizing agent, in the presence of a molibdenum complex as catalyst, preferably dioxomolibdenum (VI) bis(acetilacetonate) or dinuclear derivatives coming from its partial hydrolisis in the presence of dimethylsulfoxide, dimethylformamide or triphenylphosphine oxide. The amount of catalyst varies from 1 mol% to 10 mol%. The synthesis is performed at atmospheric pressure and the temperature varies from 15-50 ºC. The solvent used is a low molecular weight ether. The products are obtained in excellent yields and byproducts are not observed in the reaction.

Advantages

This new procedure is more efficient than other procedures described for the process. Moreover, air stands out for being the cheapest, most available, easiest to handle and safest oxidizing agent. Additionally, molibdenum catalysts are less toxic that commonly used ones, and are resistant to degradation under reaction conditions. Finally, byproduct formation is not observed and sulfones are easily isolable.

Overall, the procedure is efficient, simple, cheap, and enviromentally friendlier than previous methods.

Main Applications

Synthesis of sulfones, that can show diverse already demonstrated propierties (drugs, pesticides, materials,...). Therefore, applications in pharmaceutical and agrochemical industries.

IPR

Número de solicitud: P200703331

Fecha de solicitud: 14/12/2007

Número de patente: ES2326110B1

Fecha de concesión: 13/06/2010

Research Group

NEW METHODS IN ORGANIC SYNTHESISEste enlace se abrirá en una ventana emergente

Contact

Isabel Pinto Pascual

ipinto@ubu.esEste enlace se abrirá en una ventana emergente

+34 947 25 8895

Webmail-UBUNet

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https://correoweb.ubu.es/UBUNet

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Universidad de Burgos
Universidad de Burgos
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