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Rhodium-Catalyzed Atroposelective C–H Alkylation of 1-Aryl Isoquinoline Derivatives with Cyclopropanols

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Download Hi-Res ImageDownload to MS-PowerPointCite This:ACS Catal. 2025, 15, XXX, 4017-4024
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    Rhodium-Catalyzed Atroposelective C–H Alkylation of 1-Aryl Isoquinoline Derivatives with Cyclopropanols
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    • Wen-Wen Zhang
      Wen-Wen Zhang
      New Cornerstone Science Laboratory, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
      School of Pharmacy, Second Military Medical University (Naval Medical University), 325 Guohe Road, Shanghai 200433, China
      More by Wen-Wen Zhang
    • Quannan Wang
      Quannan Wang
      New Cornerstone Science Laboratory, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
      More by Quannan Wang
    • Chao Zheng
      Chao Zheng
      New Cornerstone Science Laboratory, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
      More by Chao Zheng
      Orcidhttps://orcid.org/0000-0002-7349-262X
    • Shu-Li You*
      Shu-Li You
      New Cornerstone Science Laboratory, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
      *Shu-Li You − New Cornerstone Science Laboratory, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China orcid.org/0000-0003-4586-8359 Email: slyou@sioc.ac.cn
      More by Shu-Li You
      Orcidhttps://orcid.org/0000-0003-4586-8359
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    ACS Catalysis

    Cite this: ACS Catal. 2025, 15, XXX, 4017–4024
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    https://doi.org/10.1021/acscatal.5c00111
    Published February 20, 2025
    © 2025 American Chemical Society
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    Abstract

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    Highly efficient synthesis of axially chiral biaryls bearing a β-aryl ketone framework is achieved by an atroposelective C–H alkylation reaction of 1-aryl isoquinoline derivatives with cyclopropanols. Judiciously choosing SPINOL-derived trisubstituted SCpRh as the catalyst is crucial for the desired asymmetric alkylation reaction over the competitive formation of alkenylation byproducts, delivering the target axially chiral biaryls in 40–99% yields and 48–97% ee. Further mechanistic studies suggested that Rh-catalyzed C–H bond cleavage serves as the turnover-limiting step, while the Cu-mediated transformation of cyclopropyl alcohols into their corresponding enones is established as the key source of the active alkylation reagents.

    © 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/acscatal.5c00111.

    • Detailed experimental procedures, theoretical calculation methods and results, characterization of new compounds, copies of 1H, 13C, 19F NMR spectra, HPLC traces, and X-ray data (PDF)

    • X-ray crystallographic data for compound 3mb (CIF)

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    Deposition Number 2401063 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via the joint Cambridge Crystallographic Data Centre (CCDC) and Fachinformationszentrum Karlsruhe Access Structures service.

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    ACS Catalysis

    Cite this: ACS Catal. 2025, 15, XXX, 4017–4024
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acscatal.5c00111
    Published February 20, 2025
    © 2025 American Chemical Society
    Request reuse permissions

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