Amine-boranes as bifunctional reagents for direct amidation of carboxylic acids
AssigneePurdue Research Foundation
InventorsPadinjaremadhom V. Ramachandran, Henry J. Hamann
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Abstract
The present invention generally relates to a process for selective and direct activation and subsequent amidation of aliphatic and aromatic carboxylic acids to afford an amide R3CONR1R2. That the process is capable of delivering gaseous or low-boiling point amines provides a major advantage over existing methodologies, which involves an intermediate of triacyloxyborane-amine complex [(R3CO2)3—B—NHR1R2]. This procedure readily produces primary, secondary, and tertiary amides, and is compatible with the chirality of the acid and amine involved. The preparation of known pharmaceutical molecules and intermediates has also been demonstrated.
Claims4
A triacyloxyborane-amine complex comprising [(R3CO2)3—B−1—N+1H(R1)R2], wherein R3 is an aryl, each of which is optionally substituted;
- R1 and R2 are, independently, hydrogen, an alkyl, or an aryl, wherein said alkyl or aryl are optionally substituted and said R1 and R2 are not both an aryl, an alkyl, or a hydrogen at the same time.
Dependencies are inferred from the claim text.