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 language | English |
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Article number | G25505ST |
Pages (from-to) | 2525-2527 |
Number of pages | 3 |
Journal | Synlett |
Issue number | 16 |
DOIs | |
State | Published - 4 Oct 2005 |
Externally published | Yes |
Keywords
- Aldehydes
- Arenes
- Electrophilic aromatic substitutions
- Oxidations
- Quinones