期刊
ENVIRONMENTAL CHEMISTRY LETTERS
卷 17, 期 2, 页码 1011-1016出版社
SPRINGER HEIDELBERG
DOI: 10.1007/s10311-018-0797-5
关键词
Reactions in water; Micellar catalysis; Passerini reaction; Autocatalysis; Green chemistry
资金
- Polish National Science Center project Harmonia [2014/14/M/ST5/00030]
- European Community COST action [CM1304]
Organic syntheses in aqueous solutions are being developed becausewater is an environmentally friendly, inexpensive, non-toxic and non-flammable solvent. The common method for the synthesis of -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 -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 findingsshowed 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 -acyloxycarboxamides that are inaccessible under standard conditions.
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