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

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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
    Southern University of Science and Technology)

  • 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
    Tsinghua University)

  • Xuenian Chen

    (School of Chemistry and Chemical Engineering, Henan Normal University
    Green Catalysis Center and College of Chemistry, Zhengzhou University)

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.

Suggested Citation

  • Yu Guo & Ruo-Ya Wang & Jia-Xin Kang & Yan-Na Ma & Cong-Qiao Xu & Jun Li & Xuenian Chen, 2021. "Efficient synthesis of primary and secondary amides via reacting esters with alkali metal amidoboranes," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-25836-5
    DOI: 10.1038/s41467-021-25836-5
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