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Hydrogen bonding template enables remote meta-C–H alkenylation of nitroarenes with electron-deficient alkenes

Author

Listed:
  • Bishal Dutta

    (Indian Institute of Technology Bombay)

  • Mayank Mahajan

    (Indian Institute of Technology Mandi)

  • Animesh Ghosh

    (Indian Institute of Technology Bombay)

  • Maciej Dajek

    (Wroclaw University of Science and Technology)

  • Rafal Kowalczyk

    (Wroclaw University of Science and Technology)

  • Bhaskar Mondal

    (Indian Institute of Technology Mandi)

  • Haibo Ge

    (Texas Tech University)

  • Debabrata Maiti

    (Indian Institute of Technology Bombay)

Abstract

Regioselective distal C−H functionalization of nitroarenes by overriding proximal C−H activation has remained an unsolved challenge. Herein, we present a palladium-catalyzed meta-C−H alkenylation of nitroarene substrate, achieved through leveraging the non-covalent hydrogen bonding interactions. Urea-based templates comprising an elongated biphenyl linker designed in such a way that it interacts with nitro group via strong hydrogen bonding interaction, while a cyano based directing group is attached along the template to coordinate with the palladium center, thereby facilitating the activation of the remote meta-C−H bond of nitrobenzene. Computational mechanistic investigation and the analysis of non-covalent interaction deciphers the crucial role of H-bonding in regulating the regioselectivity.

Suggested Citation

  • Bishal Dutta & Mayank Mahajan & Animesh Ghosh & Maciej Dajek & Rafal Kowalczyk & Bhaskar Mondal & Haibo Ge & Debabrata Maiti, 2024. "Hydrogen bonding template enables remote meta-C–H alkenylation of nitroarenes with electron-deficient alkenes," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-51764-1
    DOI: 10.1038/s41467-024-51764-1
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    References listed on IDEAS

    as
    1. Dasheng Leow & Gang Li & Tian-Sheng Mei & Jin-Quan Yu, 2012. "Activation of remote meta-C–H bonds assisted by an end-on template," Nature, Nature, vol. 486(7404), pages 518-522, June.
    2. Sukdev Bag & Sadhan Jana & Sukumar Pradhan & Suman Bhowmick & Nupur Goswami & Soumya Kumar Sinha & Debabrata Maiti, 2021. "Imine as a linchpin approach for meta-C–H functionalization," Nature Communications, Nature, vol. 12(1), pages 1-8, December.
    3. Ri-Yuan Tang & Gang Li & Jin-Quan Yu, 2014. "Conformation-induced remote meta-C–H activation of amines," Nature, Nature, vol. 507(7491), pages 215-220, March.
    Full references (including those not matched with items on IDEAS)

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