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Enantioselective Heck/Tsuji−Trost reaction of flexible vinylic halides with 1,3-dienes

Author

Listed:
  • Li-Zhi Zhang

    (Yunnan Minzu University)

  • Pei-Chao Zhang

    (Second Military Medical University (Naval Medical University))

  • Qian Wang

    (Changchun University of Technology)

  • Min Zhou

    (Yunnan Minzu University)

  • Junliang Zhang

    (Changchun University of Technology
    Fudan University)

Abstract

The enantioselective domino Heck/cross-coupling has emerged as a powerful tool in modern chemical synthesis for decades. Despite significant progress in relative rigid skeleton substrates, the implementation of asymmetric Heck/cross-coupling cascades of highly flexible haloalkene substrates remains a challenging and and long-standing goal. Here we report an efficient asymmetric domino Heck/Tsuji−Trost reaction of highly flexible vinylic halides with 1,3-dienes enabled by palladium catalysis. Specifically, the Heck insertion as stereodetermining step to form ƞ3 allyl palladium complex and in situ trapping with nucleophiles enable efficient Heck/etherification in a formal (4 + 2) cycloaddition manner. Engineering the Sadphos bearing androgynous non-C2-symmetric chiral sulfinamide phosphine ligands are vital component in achieving excellent catalytic reactivity and enantioselectivity. This strategy offers a general, modular and divergent platform for rapidly upgrading feedstock flexible vinylic halides and dienes to various value-added molecules and is expected to inspire the development of other challenging enantioselective domino Heck/cross-couplings.

Suggested Citation

  • Li-Zhi Zhang & Pei-Chao Zhang & Qian Wang & Min Zhou & Junliang Zhang, 2025. "Enantioselective Heck/Tsuji−Trost reaction of flexible vinylic halides with 1,3-dienes," Nature Communications, Nature, vol. 16(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-56142-z
    DOI: 10.1038/s41467-025-56142-z
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    References listed on IDEAS

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    1. Shuai Zhu & Zihao Ye & Ming-Jie Chen & Lei Wang & Yu-Zhuo Wang & Ke-Nan Zhang & Wen-Bo Li & Han-Ming Ding & Zhiming Li & Junliang Zhang, 2023. "Mechanistic study on the side arm effect in a palladium/Xu-Phos-catalyzed enantioselective alkoxyalkenylation of γ-hydroxyalkenes," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
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