Development of a Metal-Free Oxidation of Alcohols with Dimethyl Sulfoxide (DMSO) Activated by Tosyl Chloride

Abstract

In this article we propose an efficient metal-free method for the mild oxidation of alcohols using dimethyl sulfoxide/tosyl chloride at ambient temperature. The procedure described here is an easy and practical method for the oxidation of primary, secondary, allylic, and benzylic alcohols into their corresponding aldehydes and ketones. The notable advantages of this protocol are mild reaction conditions, good yields and selectivity, and simple workup with minimal waste containing no metallic components. The mechanism of the transformation is also investigated.

GRAPHICAL ABSTRACT

Keywords:

• Alcohol
• aldehyde
• dimethyl sulfoxide
• ketone
• metal-free
• oxidation
• tosyl chloride

Notes

^a Conditions: Substrate, DMSO/TsCl 1:3:1.5 (molar ratio), (CH₃CH₂)₃N (3 mmol), toluene as solvent, rt.

^b After addition of triethylamine.

^c GC yield.

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