Efficient synthesis of primary and secondary amides via reacting esters with alkali metal amidoboranes

Yu Guo, Ruo-Ya Wang, Jia-Xin Kang, Yan-Na Ma, Cong-Qiao Xu, Jun Li () and Xuenian Chen ()
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Yu Guo: School of Chemistry and Chemical Engineering, Henan Normal University
Ruo-Ya Wang: School of Chemistry and Chemical Engineering, Henan Normal University
Jia-Xin Kang: School of Chemistry and Chemical Engineering, Henan Normal University
Yan-Na Ma: Green Catalysis Center and College of Chemistry, Zhengzhou University
Cong-Qiao Xu: Southern University of Science and Technology
Jun Li: Southern University of Science and Technology
Xuenian Chen: School of Chemistry and Chemical Engineering, Henan Normal University

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract Amides are one of the most important organic compounds that are widely applied in medicine, biochemistry, and materials science. To find an efficient synthetic method of amides is a challenge for organic chemistry. We report here a facile synthesis method of primary and secondary amides through a direct amidation of esters with sodium amidoboranes (NaNHRBH3, R = H, Me), at room temperature without using catalysts and other reagents. This process is rapid and chemoselective, and features quantitative conversion and wide applicability for esters tolerating different functional groups. The experimental and theoretical studies reveal a reaction mechanism with nucleophilic addition followed by a swift proton transfer-induced elimination reaction.

Date: 2021
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DOI: 10.1038/s41467-021-25836-5

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