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RESEARCH PRODUCT
ChemInform Abstract: Nucleophilic Benzoylation Using Lithiated Methyl Mandelate as a Synthetic Equivalent of the Benzoyl Carbanion. Oxidative Decarboxylation of α-Hydroxyacids.
Belen MonjeGonzalo BlayJosé R. PedroPilar FormentinRafael RuizIsabel Fernándezsubject
chemistry.chemical_classificationchemistry.chemical_compoundNucleophileChemistryArylOrganic chemistryGeneral MedicineAlkylationAlkylOxidative decarboxylationUmpolungCatalysisCarbaniondescription
Abstract The synthesis of alkyl aryl ketones using lithiated methyl mandelate as a synthetic equivalent of the benzoyl carbanion is reported (Umpolung). The methodology involves alkylation of methyl mandelate, hydrolysis of the ester group and oxidative decarboxylation of the resulting α-hydroxyacids. The last step is carried out in a catalytic aerobic way using a Co(III) complex in the presence of pivalaldehyde under very mild and advantageous conditions. The procedure is also applied to methyl mandelates substituted on the aromatic ring.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2010-05-26 | ChemInform |