Aerobic oxidation of alkenes to esters of vicinal diols with a syn-configuration catalyzed by I2 and the H5PV 2Mo10O40 polyoxometalate

Olena Branytska, Ronny Neumann

Research output: Contribution to journalArticle

6 Citations (Scopus)

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.

Original languageEnglish
Article numberG25505ST
Pages (from-to)2525-2527
Number of pages3
JournalSynlett
Issue number16
DOIs
Publication statusPublished - Oct 4 2005

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Keywords

  • Aldehydes
  • Arenes
  • Electrophilic aromatic substitutions
  • Oxidations
  • Quinones

ASJC Scopus subject areas

  • Organic Chemistry

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