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Amine-boranes as Dual-Purpose Reagents for Direct Amidation of Carboxylic Acids
P Veeraraghavan Ramachandran1, Henry J Hamann1, Shivani Choudhary1
1Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, United States.
Abstract:
Amine-boranes serve as dual-purpose reagents for direct amidation, activating aliphatic and aromatic carboxylic acids and, subsequently, delivering amines to provide the corresponding amides in up to 99% yields. Delivery of gaseous or low-boiling amines as their borane complexes provides a major advantage over existing methodologies. Utilizing amine-boranes containing borane incompatible functionalities allows for the preparation of functionalized amides. An intermolecular mechanism proceeding through a triacyloxyborane-amine complex is proposed.
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