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SET activation of nitroarenes by 2-azaallyl anions as a straightforward access to 2,5-dihydro-1,2,4-oxadiazoles

Author

Listed:
  • Dong Zou

    (Zhejiang University City College)

  • Lishe Gan

    (Wuyi University)

  • Fan Yang

    (Zhejiang University City College)

  • Huan Wang

    (Zhejiang University City College)

  • Youge Pu

    (University of Pennsylvania)

  • Jie Li

    (Zhejiang University City College)

  • Patrick J. Walsh

    (University of Pennsylvania)

Abstract

The use of nitroarenes as amino sources in synthesis is challenging. Herein is reported an unusual, straightforward, and transition metal-free method for the net [3 + 2]-cycloaddition reaction of 2-azaallyl anions with nitroarenes. The products of this reaction are diverse 2,5-dihydro-1,2,4-oxadiazoles (>40 examples, up to 95% yield). This method does not require an external reductant to reduce nitroarenes, nor does it employ nitrosoarenes, which are often used in N–O cycloadditions. Instead, it is proposed that the 2-azaallyl anions, which behave as super electron donors (SEDs), deliver an electron to the nitroarene to generate a nitroarene radical anion. A downstream 2-azaallyl radical coupling with a newly formed nitrosoarene is followed by ring closure to afford the observed products. This proposed reaction pathway is supported by computational studies and experimental evidence. Overall, this method uses readily available materials, is green, and exhibits a broad scope.

Suggested Citation

  • Dong Zou & Lishe Gan & Fan Yang & Huan Wang & Youge Pu & Jie Li & Patrick J. Walsh, 2021. "SET activation of nitroarenes by 2-azaallyl anions as a straightforward access to 2,5-dihydro-1,2,4-oxadiazoles," Nature Communications, Nature, vol. 12(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-26767-x
    DOI: 10.1038/s41467-021-26767-x
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    Cited by:

    1. Zhen Zhang & Shusheng Yue & Bo Jin & Ruchun Yang & Shengchun Wang & Tianqi Zhang & Li Sun & Aiwen Lei & Hu Cai, 2024. "Para-selective nitrobenzene amination lead by C(sp2)-H/N-H oxidative cross-coupling through aminyl radical," Nature Communications, Nature, vol. 15(1), pages 1-9, December.

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