Abstract
Organic syntheses in aqueous solutions are being developed because water is an environmentally friendly, inexpensive, non-toxic and non-flammable solvent. The common method for the synthesis of α-acyloxycarboxamides is the one-pot three-component condensation of a carboxylic acid, an aldehyde and an isocyanide, entitled the Passerini reaction. This reaction is usually performed in organic solvents such as dichloromethane or toluene. Herein we report a novel protocol for the synthesis of α-acyloxycarboxamides in aqueous solution under mild reaction conditions, for which one of the reactants, the carboxylic acid, is a micelle- or vesicle-forming compound. The reaction is carried out successfully with up to 93% yield in an aqueous solution without catalyst or surfactant addition. Our findings showed that the fatty acid used as a substrate accelerates the reaction due to its self-assembly properties. This environmentally benign protocol has several advantages such as high yields, mild reaction conditions and easy workup. Moreover, it allows to synthesize α-acyloxycarboxamides that are inaccessible under standard conditions.
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Acknowledgements
We gratefully acknowledge the financial support of the Polish National Science Center project Harmonia No 2014/14/M/ST5/00030 and the European Community COST action CM1304 for providing a stimulating environment which led to this collaborative research.
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Paprocki, D., Wilk, M., Madej, A. et al. Catalyst-free synthesis of α-acyloxycarboxamides in aqueous media. Environ Chem Lett 17, 1011–1016 (2019). https://doi.org/10.1007/s10311-018-0797-5
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DOI: https://doi.org/10.1007/s10311-018-0797-5