Transformation of alcohols to esters promoted by hydrogen bonds using oxygen as the oxidant under metal-free conditions.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 30310866.
- Also identified by DOI 10.1126/sciadv.aas9319 and PMC identifier 6173529.
- Licence recorded as CC BY-NC.
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Abstract
One-pot oxidative transformation of alcohols into esters is very attractive, but metal-based catalysts are used in the reported routes. We discovered that the basic ionic liquid 1-ethyl-3-methylimidazolium acetate ([EMIM] OAc) could effectively catalyze this kind of reaction using O<sub>2</sub> as an oxidant without any other catalysts or additives. The oxidative self-esterification of benzylic alcohols or aliphatic alcohols and cross-esterification between benzyl alcohols and aliphatic alcohols could all be achieved with high yields. Detailed study revealed that the cation with acidic proton and basic acetate anion could simultaneously form multiple hydrogen bonds with the hydroxyl groups of the alcohols, which catalyzed the reaction very effectively. As far as we know, this is the first work to carry out this kind of reaction under metal-free conditions.