Rapid Synthesis of Primary Amides Using Ammonia Borane

Xiao-Yun Li; Jia-Xin Kang; Hui Han; Yan-Na Ma; Zhenxing Liu; Xuenian Chen

doi:10.1021/acs.joc.4c02710

Rapid Synthesis of Primary Amides Using Ammonia Borane

J Org Chem. 2025 Jan 23. doi: 10.1021/acs.joc.4c02710. Online ahead of print.

Authors

Xiao-Yun Li¹, Jia-Xin Kang², Hui Han¹, Yan-Na Ma¹, Zhenxing Liu¹, Xuenian Chen^{1

2}

Affiliations

¹ College of Chemistry, Zhengzhou University, Zhengzhou 450001, China.
² School of Chemistry and Chemical Engineering, Henan Key Laboratory of Boron Chemistry and Advanced Materials, Henan Normal University, Xinxiang 453007, China.

PMID: 39846305
DOI: 10.1021/acs.joc.4c02710

Abstract

We report the rapid synthesis of primary amides by directly using commercially available ammonia borane (NH₃·BH₃), sodium hexamethyldisilazide (NaHMDS), and esters. The success of this protocol relies on NH₃·BH₃ as the nitrogen source being considerably more convenient and NaHMDS being an excellent proton abstractor but not participating in the nucleophilic addition reaction. The reaction had a wide substrate scope containing bioactive molecules, and most of the substrates were efficiently amidated over 90% yields.