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Nickel-catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes

Author

Listed:
  • Wei-Song Zhang

    (Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Ding-Wei Ji

    (Chinese Academy of Sciences)

  • Ying Li

    (Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Xiang-Xin Zhang

    (Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Yong-Kang Mei

    (Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Bing-Zhi Chen

    (Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Qing-An Chen

    (Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

Abstract

Developing efficient strategies to realize divergent arylation of dienes has been a long-standing synthetic challenge. Herein, a nickel catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes has been demonstrated through the regulation of ligands and additives. In the presence of Mn/NEt3, the Mizoroki–Heck reaction of dienes delivers linear products under Ni(dppe)Cl2 catalysis in high regio- and stereoselectivities. With the help of catalytic amount of organoboron and NaF, the use of bulky ligand IPr diverts the selectivity from linear products to branched products. Highly aryl-substituted compounds can be transformed from dispersive Mizoroki–Heck products programmatically. Preliminary experimental studies are carried out to elucidate the role of additives.

Suggested Citation

  • Wei-Song Zhang & Ding-Wei Ji & Ying Li & Xiang-Xin Zhang & Yong-Kang Mei & Bing-Zhi Chen & Qing-An Chen, 2023. "Nickel-catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-36237-1
    DOI: 10.1038/s41467-023-36237-1
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