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Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids

P. Veeraraghavan Ramachandran* and Henry J. Hamann

*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, Org. Lett., 2021, 23, 2938-2942.

DOI: 10.1021/acs.orglett.1c00591 (free Supporting Information)


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Abstract

Ammonia-borane serves as an efficient precatalyst for the direct amidation of both aromatic and aliphatic carboxylic acids. This method is efficient with equimolar amounts of the coupling partners and offers high functional group tolerance and chromatography-free purification.


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Reaction intermediate IV can react as an electrophile (IV-a) or a nucleophile (IV-b)



Key Words

amides


ID: J54-Y2021