Amine-boranes as Dual-Purpose Reagents for Direct Amidation of Carboxylic Acids

Org Lett. 2020 Nov 6;22(21):8593-8597. doi: 10.1021/acs.orglett.0c03184. Epub 2020 Oct 27.

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.

Publication types

  • Research Support, Non-U.S. Gov't