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Remote-carbonyl-directed sequential Heck/isomerization/C(sp2)–H arylation of alkenes for modular synthesis of stereodefined tetrasubstituted olefins

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  • Runze Luan

    (Chinese Academy of Sciences
    Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China
    University of Chinese Academy of Sciences)

  • Ping Lin

    (Chinese Academy of Sciences
    Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China)

  • Kun Li

    (Chinese Academy of Sciences
    Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China
    Fujian Normal University)

  • Yu Du

    (Chinese Academy of Sciences
    Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China
    University of Chinese Academy of Sciences
    Fujian Normal University)

  • Weiping Su

    (Chinese Academy of Sciences
    Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China
    University of Chinese Academy of Sciences
    Fujian Normal University)

Abstract

Modular and regio-/stereoselective syntheses of all-carbon tetrasubstituted olefins from simple alkene materials remain a challenging project. Here, we demonstrate that a remote-carbonyl-directed palladium-catalyzed Heck/isomerization/C(sp2)–H arylation sequence enables unactivated 1,1-disubstituted alkenes to undergo stereoselective terminal diarylation with aryl iodides, thus offering a concise approach to construct stereodefined tetrasubstituted olefins in generally good yields under mild conditions; diverse carbonyl groups are allowed to act as directing groups, and various aryl groups can be introduced at the desired position simply by changing aryl iodides. The stereocontrol of the protocol stems from the compatibility between the E/Z isomerization and the alkenyl C(sp2)–H arylation, where the vicinal group-directed C(sp2)–H arylation of the Z-type intermediate product thermodynamically drives the reversible E to Z isomerization. Besides, the carbonyl group not only promotes the Pd-catalyzed sequential transformations of unactivated alkenes by weak coordination, but also avoids byproducts caused by other possible β-H elimination.

Suggested Citation

  • Runze Luan & Ping Lin & Kun Li & Yu Du & Weiping Su, 2024. "Remote-carbonyl-directed sequential Heck/isomerization/C(sp2)–H arylation of alkenes for modular synthesis of stereodefined tetrasubstituted olefins," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-46051-y
    DOI: 10.1038/s41467-024-46051-y
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    References listed on IDEAS

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    1. Shubham Dutta & Shashank Shandilya & Shengwen Yang & Manash Protim Gogoi & Vincent Gandon & Akhila K. Sahoo, 2022. "Cationic-palladium catalyzed regio- and stereoselective syn-1,2-dicarbofunctionalization of unsymmetrical internal alkynes," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    2. Yantao Li & Qianzhen Shao & Hengchi He & Chengjian Zhu & Xiao-Song Xue & Jin Xie, 2022. "Highly selective synthesis of all-carbon tetrasubstituted alkenes by deoxygenative alkenylation of carboxylic acids," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
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