Cleavage of Carboxylic Esters by Aluminum and Iodine
Dayong Sang, Huaxin Yue, Fu Yang, Juan Tian
Abstract
A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.
Topics & Concepts
ChemistryArylAnhydrousAcetonitrileCarboxylic acidAlkylAcetylationCleavage (geology)IodineOrganic chemistryBiochemistryGeotechnical engineeringEngineeringFracture (geology)GeneChemical Synthesis and ReactionsChemical Synthesis and AnalysisAsymmetric Synthesis and Catalysis