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Diversity-oriented synthesis of stereodefined tetrasubstituted alkenes via a modular alkyne gem-addition strategy

Author

Listed:
  • Xuan Di

    (Nanjing University of Chinese Medicine)

  • Sitian Zhou

    (Nanjing University)

  • Yali Qin

    (Nanjing University of Chinese Medicine)

  • Wenjun Li

    (Nanjing University of Chinese Medicine)

  • Yue Zhang

    (Nanjing University of Chinese Medicine)

  • Jie Zhang

    (Nanjing University of Chinese Medicine)

  • Xu Shen

    (Nanjing University of Chinese Medicine)

  • Jie Han

    (Nanjing University)

  • Jin Xie

    (Nanjing University
    China Pharmaceutical University)

  • Hongming Jin

    (Nanjing University of Chinese Medicine
    Nanjing University of Chinese Medicine)

Abstract

Stereocontrolled construction of tetrasubstituted olefins has been an attractive issue yet remains challenging for synthetic chemists. In this manuscript, alkynyl selenides, when treated with ArBCl2, are subject to an exclusive 1,1-carboboration, affording tetrasubstituted alkenes with excellent levels of E-selectivity. Detailed mechanistic studies, supported by DFT calculations, elucidates the role of selenium in this 1,1-addition process. Coupled with subsequent C-B and C-Se bond transformations, this 1,1-addition protocol constitutes a modular access to stereodefined all-carbon tetrasubstituted alkenes. The merit of this approach is demonstrated by programmed assembly of diverse functionalized multi-arylated alkenes, especially enabling the stereospecific synthesis of all six possible stereoisomers of tetraarylethene (TAE) derived from the random permutation of four distinct aryl substituents around the double bond. The diversity-oriented synthesis is further utilized to explore different TAE luminogenic properties and potential Se-containing antitumor lead compounds.

Suggested Citation

  • Xuan Di & Sitian Zhou & Yali Qin & Wenjun Li & Yue Zhang & Jie Zhang & Xu Shen & Jie Han & Jin Xie & Hongming Jin, 2025. "Diversity-oriented synthesis of stereodefined tetrasubstituted alkenes via a modular alkyne gem-addition strategy," Nature Communications, Nature, vol. 16(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-56184-3
    DOI: 10.1038/s41467-025-56184-3
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    References listed on IDEAS

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    1. Zijian Fang & Giuditta Corbizi Fattori & Thomas McKerrell & Rebecca H. Boucher & Aimee Jackson & Rachel S. Fletcher & Dorian Forte & Jose-Ezequiel Martin & Sonia Fox & James Roberts & Rachel Glover & , 2023. "Tamoxifen for the treatment of myeloproliferative neoplasms: A Phase II clinical trial and exploratory analysis," Nature Communications, Nature, vol. 14(1), pages 1-21, December.
    2. Warren R.J.D. Galloway & Albert Isidro-Llobet & David R. Spring, 2010. "Diversity-oriented synthesis as a tool for the discovery of novel biologically active small molecules," Nature Communications, Nature, vol. 1(1), pages 1-13, December.
    3. Xun-Shen Liu & Zhiqiong Tang & Zhiming Li & Mingjia Li & Lin Xu & Lu Liu, 2021. "Modular and stereoselective synthesis of tetrasubstituted vinyl sulfides leading to a library of AIEgens," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    4. Yoshiaki Shoji & Naoki Tanaka & Sho Muranaka & Naoki Shigeno & Haruka Sugiyama & Kumiko Takenouchi & Fatin Hajjaj & Takanori Fukushima, 2016. "Boron-mediated sequential alkyne insertion and C–C coupling reactions affording extended π-conjugated molecules," Nature Communications, Nature, vol. 7(1), pages 1-7, November.
    5. Cheng-Long Ji & Hongliang Chen & Qi Gao & Jie Han & Weipeng Li & Jin Xie, 2024. "Dinuclear gold-catalyzed divergent dechlorinative radical borylation of gem-dichloroalkanes," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
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