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Protecting-Group-Free Mechanosynthesis of Amides from Hydroxycarboxylic Acids

Gallou, Fabrice (2024) Protecting-Group-Free Mechanosynthesis of Amides from Hydroxycarboxylic Acids. RSC Mechanochemistry, 1. pp. 189-195.


Mechanochemical methods for assembling carbon-nitrogen bonds play a central role in the ongoing green chemistry-driven renovation of organic synthesis.However, there is a paucity of reports addressing chemoselective issues in these transformations, such as the tolerance of unmasked hydroxyl groups. Screening of various amide coupling conditions revealed 1 ethyl 3 (3 dimethylaminopropyl)carbodiimide (EDC) in combination with ethyl acetate as a liquid-assisted grinding (LAG) solvent as the most selective amide coupler, delivering 76–94% yields of the respective amide products from unprotected hydroxycarboxylic acids. Boc-protected tyrosine and serine with unmasked OH functionalities were successfully involved in peptide couplings.

Item Type: Article
Date Deposited: 04 Jun 2024 00:46
Last Modified: 04 Jun 2024 00:46