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

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.

aldehydes - arenes - electrophilic aromatic substitutions - oxidations - quinones

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