4.6 Article

Amide bond formation in aqueous solution: direct coupling of metal carboxylate salts with ammonium salts at room temperature

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ORGANIC & BIOMOLECULAR CHEMISTRY
卷 19, 期 46, 页码 10073-10080

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob02064a

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  1. PHENIKAA University Foundation for Science and Technology Development

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The study presents a green, rapid, and simple method for direct coupling of carboxylate salts and ammonium salts at room temperature without the addition of tertiary amine bases, utilizing a water-soluble coupling reagent EDC·HCl. The reaction tolerates both carboxylate and amine salts, providing a clean product without column chromatography, and can be used as an alternative method in laboratory and industrial scales.
Herein, we report a green, expeditious, and practically simple protocol for direct coupling of carboxylate salts and ammonium salts under ACN/H2O conditions at room temperature without the addition of tertiary amine bases. The water-soluble coupling reagent EDC center dot HCl is a key component in the reaction. The reaction runs smoothly with unsubstituted/substituted ammonium salts and provides a clean product without column chromatography. Our reaction tolerates both carboxylate (which are unstable in other forms) and amine salts (which are unstable/volatile when present in free form). We believe that the reported method could be used as an alternative and suitable method at the laboratory and industrial scales.

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