Amine-boranes act as dual-purpose reagents for the direct amidation of carboxylic acids. These reagents activate both aliphatic and aromatic carboxylic acids, and subsequently deliver amines to provide the corresponding amides in up to 99% yields with excellent chemoselectivity. This protocol offers several advantages over the current amidation procedures involving hazardous or unstable reagents with low functional group tolerance. It has a major advantage over other methodologies in that even gaseous or low-boiling amines, such as ammonia, methylamine, allylamine, etc. can be delivered as liquid or solid borane complexes. Employment of our recent synthesis of functionalized amine-boranes allows for the preparation of functionalized amides. This amidation protocol can be readily performed at mole-scale and has been demonstrated for the preparation of several bio-active molecules.

Amine-boranes as dual-purpose reagents for direct amidation of carboxylic acids

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.