Amine-boranes as Dual-Purpose Reagents for Direct Amidation of Carboxylic Acids
P. Veeraraghavan Ramachandran, Henry J. Hamann, Shivani Choudhary
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.
Topics & Concepts
BoranesChemistryAmine gas treatingReagentBoraneOrganic chemistryCombinatorial chemistryCatalysisBoronChemical Synthesis and AnalysisChemical Synthesis and ReactionsOrganoboron and organosilicon chemistry