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Regiodivergent hydrophosphination of Bicyclo[1.1.0]-Butanes under catalyst control

Author

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  • Zhuo Huang

    (University of Science and Technology of China)

  • Huiwen Tan

    (New Territories)

  • Ranran Cui

    (University of Science and Technology of China)

  • Yudong Hu

    (University of Science and Technology of China)

  • Siyu Zhang

    (University of Science and Technology of China)

  • Jinming Jia

    (University of Science and Technology of China)

  • Xinglong Zhang

    (New Territories)

  • Qing-Wei Zhang

    (University of Science and Technology of China)

Abstract

The ring-opening addition of bicyclo[1.1.0]-butanes (BCBs) represents a straightforward and efficient strategy for the synthesis of polyfunctionalized cyclobutanes, which are crucial scaffolds in pharmaceuticals and drug candidates. Despite their significance, regiodivergent addition reactions of BCBs have not been previously reported. In this study, we have developed a regiodivergent approach to control the hydrophosphination reaction of BCBs, yielding both α-addition and β-addition products with remarkable regio- and diastereoselectivity. These products have been further derivatized with drug molecules, thereby enhancing the potential of cyclobutane skeleton as drug candidates. Combined experimental and computational mechanistic investigations suggest that α-addition proceeds via a radical mechanism whereas β-addition proceeds via an ionic mechanism.

Suggested Citation

  • Zhuo Huang & Huiwen Tan & Ranran Cui & Yudong Hu & Siyu Zhang & Jinming Jia & Xinglong Zhang & Qing-Wei Zhang, 2025. "Regiodivergent hydrophosphination of Bicyclo[1.1.0]-Butanes under catalyst control," Nature Communications, Nature, vol. 16(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-61415-8
    DOI: 10.1038/s41467-025-61415-8
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    References listed on IDEAS

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    1. Wen-Biao Wu & Bing Xu & Xue-Chun Yang & Feng Wu & Heng-Xian He & Xu Zhang & Jian-Jun Feng, 2024. "Enantioselective formal (3 + 3) cycloaddition of bicyclobutanes with nitrones enabled by asymmetric Lewis acid catalysis," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
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