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

P. Veeraraghavan Ramachandran*, Henry J. Hamann and Shivani Choudhary

*Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, United States, Email: chandranpurdue.edu

P. V. Ramachandran, H. J. Hamann, S. Choudhary, Org. Lett., 2020, 22, 8593-8597.

DOI: 10.1021/acs.orglett.0c03184 (free Supporting Information)


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Abstract

The reaction of amine-boranes as dual-purpose reagents with aliphatic and aromatic carboxylic acids provides amides in very good yields. Delivery of gaseous or low-boiling amines as their borane complexes provides a major advantage over existing methodologies.

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proposed mechanism



Key Words

amides


ID: J54-Y2020