Aerobic Oxidation of Alkenes to Esters of Vicinal Diols with a syn-Configuration Catalyzed by I2 and the H5PV2Mo10O40 Polyoxometalate

Olena Branytska; Ronny Neumann

doi:10.1055/s-2005-917069

LETTER

Aerobic Oxidation of Alkenes to Esters of Vicinal Diols with a syn-Configuration Catalyzed by I₂ and the H₅PV₂Mo₁₀O₄₀ Polyoxometalate

Olena Branytska, Ronny Neumann*
Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, 76100, Israel
Fax: +972(8)9344142; e-Mail: Ronny.Neumann@weizman.ac.il;

Abstract

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Abstract

A new method for the synthesis of vicinal diols from alkenes has been developed. Reaction of molecular iodine in the presence of a polyoxometalate as oxidation catalyst under aerobic conditions in acetic acid solvent leads to the oxidative iodoacetoxylation of an alkene, i.e. formation of a 1,2-iodoacetate. Further in situ substitution of the iodide by water yields the 1,2-diol monoacetate with a predominantly (ca. 4.5:1) cis-configuration. Further esterification under the reaction’s acidic conditions leads also to the cis-diacetate. The method may be valuable for the synthesis of cis-vicinal diols without use of toxic osmium catalysts.

Key words

aldehydes - arenes - electrophilic aromatic substitutions - oxidations - quinones

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References

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