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Direct amidation of esters with nitroarenes

Author

Listed:
  • Chi Wai Cheung

    (Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), ISIC-LSCI, BCH 3305)

  • Marten Leendert Ploeger

    (Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), ISIC-LSCI, BCH 3305)

  • Xile Hu

    (Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), ISIC-LSCI, BCH 3305)

Abstract

Esters are one of the most common functional groups in natural and synthetic products, and the one-step conversion of the ester group into other functional groups is an attractive strategy in organic synthesis. Direct amidation of esters is particularly appealing due to the omnipresence of the amide moiety in biomolecules, fine chemicals, and drug candidates. However, efficient methods for direct amidation of unactivated esters are still lacking. Here we report nickel-catalysed reductive coupling of unactivated esters with nitroarenes to furnish in one step a wide range of amides bearing functional groups relevant to the development of drugs and agrochemicals. The method has been used to expedite the syntheses of bio-active molecules and natural products, as well as their post-synthetic modifications. Preliminary mechanistic study indicates a reaction pathway distinct from conventional amidation methods using anilines as nitrogen sources. The work provides a novel and efficient method for amide synthesis.

Suggested Citation

  • Chi Wai Cheung & Marten Leendert Ploeger & Xile Hu, 2017. "Direct amidation of esters with nitroarenes," Nature Communications, Nature, vol. 8(1), pages 1-10, April.
    • Handle: RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_ncomms14878
    DOI: 10.1038/ncomms14878
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    Cited by:

    1. Jie Gao & Rui Ma & Fairoosa Poovan & Lan Zhang & Hanan Atia & Narayana V. Kalevaru & Wenjing Sun & Sebastian Wohlrab & Denis A. Chusov & Ning Wang & Rajenahally V. Jagadeesh & Matthias Beller, 2023. "Streamlining the synthesis of amides using Nickel-based nanocatalysts," Nature Communications, Nature, vol. 14(1), pages 1-13, December.
    2. Shuaishuai Wang & Tingrui Li & Chengyihan Gu & Jie Han & Chuan-Gang Zhao & Chengjian Zhu & Hairen Tan & Jin Xie, 2022. "Decarboxylative tandem C-N coupling with nitroarenes via SH2 mechanism," Nature Communications, Nature, vol. 13(1), pages 1-10, December.

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