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C(alkyl)–C(vinyl) bond cleavage enabled by Retro-Pallada-Diels-Alder reaction

Author

Listed:
  • Qingyang Zhao

    (Northwest University
    Shenzhen Campus of Sun Yat-sen University)

  • Le Yu

    (Northwest University)

  • Yao-Du Zhang

    (Northwest University)

  • Yong-Qiang Guo

    (Northwest University)

  • Ming Chen

    (Northwest University)

  • Zhi-Hui Ren

    (Northwest University)

  • Zheng-Hui Guan

    (Northwest University)

Abstract

Activation and cleavage of carbon–carbon (C–C) bonds is a fundamental transformation in organic chemistry while inert C–C bonds cleavage remains a long-standing challenge. Retro-Diels-Alder (retro-DA) reaction is a well-known and important tool for C–C bonds cleavage but less been explored in methodology by contrast to other strategies. Herein, we report a selective C(alkyl)–C(vinyl) bond cleavage strategy realized through the transient directing group mediated retro-Diels-Alder reaction of a six-membered palladacycle, which is obtained from an in situ generated hydrazone and palladium hydride species. This unprecedented strategy exhibits good tolerances and thus offers new opportunities for late-stage modifications of complex molecules. DFT calculations revealed that an intriguing retro-Pd(IV)-Diels-Alder process is possibly involved in the catalytic cycle, thus bridging both Retro-Diels-Alder reaction and C–C bond cleavage. We anticipate that this strategy should prove instrumental for potential applications to achieve the modification of functional organic skeletons in synthetic chemistry and other fields involving in molecular editing.

Suggested Citation

  • Qingyang Zhao & Le Yu & Yao-Du Zhang & Yong-Qiang Guo & Ming Chen & Zhi-Hui Ren & Zheng-Hui Guan, 2023. "C(alkyl)–C(vinyl) bond cleavage enabled by Retro-Pallada-Diels-Alder reaction," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-38067-7
    DOI: 10.1038/s41467-023-38067-7
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    References listed on IDEAS

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    1. Ying Xia & Gang Lu & Peng Liu & Guangbin Dong, 2016. "Catalytic activation of carbon–carbon bonds in cyclopentanones," Nature, Nature, vol. 539(7630), pages 546-550, November.
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    Cited by:

    1. Fei Wu & Bo Wang & Na-Qi Li & Hui-Yi Yang & Zhi-Hui Ren & Zheng-Hui Guan, 2023. "Palladium-catalyzed regiodivergent hydrochlorocarbonylation of alkenes for formation of acid chlorides," Nature Communications, Nature, vol. 14(1), pages 1-9, December.

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