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Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids
P Veeraraghavan Ramachandran1, Henry J Hamann1
1Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, United States.
Abstract:
Ammonia-borane serves as an efficient substoichiometric (10%) precatalyst for the direct amidation of both aromatic and aliphatic carboxylic acids. In situ generation of amine-boranes precedes the amidation and, unlike the amidation with stoichiometric amine-boranes, this process is facile with 1 equiv of the acid. This methodology has high functional group tolerance and chromatography-free purification but is not amenable for esterification. The latter feature has been exploited to prepare hydroxyl- and thiol-containing amides.
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