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Microwave-Assisted Synthesis of Heterocycles via Rhodium(III)-Catalyzed C–H Activation: Norbornadiene as an Acetylene Equivalent
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    Microwave-Assisted Synthesis of Heterocycles via Rhodium(III)-Catalyzed C–H Activation: Norbornadiene as an Acetylene Equivalent
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    • Joyann S. Donaldson
      Joyann S. Donaldson
      Pfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United States
    • Haojun Jiang
      Haojun Jiang
      BioDuro, No. 233 North FuTe Road, WaiGaoQiao Free Trade Zone, Shanghai 200131, P. R. China
      More by Haojun Jiang
    • Dehuan Kong
      Dehuan Kong
      BioDuro, No. 233 North FuTe Road, WaiGaoQiao Free Trade Zone, Shanghai 200131, P. R. China
      More by Dehuan Kong
    • Wei Li
      Wei Li
      BioDuro, No. 233 North FuTe Road, WaiGaoQiao Free Trade Zone, Shanghai 200131, P. R. China
      More by Wei Li
    • Indrawan J. McAlpine
      Indrawan J. McAlpine
      Pfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United States
    • Sajiv K. Nair
      Sajiv K. Nair
      Pfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United States
    • Sylvie Sakata
      Sylvie Sakata
      Pfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United States
    • Jillian E. Spangler
      Jillian E. Spangler
      Pfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United States
    • Nicole Sun
      Nicole Sun
      BioDuro, No. 233 North FuTe Road, WaiGaoQiao Free Trade Zone, Shanghai 200131, P. R. China
      More by Nicole Sun
    • Michelle B. Tran-Dubé
      Michelle B. Tran-Dubé
      Pfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United States
    • Yang Zhou
      Yang Zhou
      BioDuro, No. 233 North FuTe Road, WaiGaoQiao Free Trade Zone, Shanghai 200131, P. R. China
      More by Yang Zhou
    • Ryan L. Patman*
      Ryan L. Patman
      Pfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United States
      *E-mail: [email protected]
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    Organic Letters

    Cite this: Org. Lett. 2025, 27, 3, 728–733
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    https://doi.org/10.1021/acs.orglett.4c04334
    Published January 10, 2025
    Copyright © 2025 American Chemical Society

    Abstract

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    General procedures for the rhodium-catalyzed annulation of aryl/heteroaryl O-pivaloyl hydroxamic acids and norbornadiene have been developed. Employing norbornadiene as an acetylene equivalent enables utilization of diverse heterocyclic substrates for this transformation which fail to react or undergo competitive Lossen rearrangement under previously reported conditions. Microwave heating significantly reduces reaction times compared to conventional protocols and allows a one-step process to be realized. The conditions described herein have been adapted for gram-scale synthesis and applied to the formal synthesis of Pfizer clinical candidates.

    Copyright © 2025 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.4c04334.

    • Experimental procedures; characterization data and copies of NMR spectra for all novel compounds (PDF)

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    Organic Letters

    Cite this: Org. Lett. 2025, 27, 3, 728–733
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.4c04334
    Published January 10, 2025
    Copyright © 2025 American Chemical Society

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