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Organoelectrocatalytic cyclopropanation of alkenyl trifluoroborates with methylene compounds

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  • Wei Yi

    (Nanjing Forestry University)

  • Peng-Cheng Xu

    (Nanjing Forestry University)

  • Tianyu He

    (Nanjing Forestry University)

  • Shuai Shi

    (Nanjing Forestry University)

  • Shenlin Huang

    (Nanjing Forestry University
    Hunan Normal University)

Abstract

Cyclopropanes are not only privileged motifs in many natural products, agrochemicals, and pharmaceuticals, but also highly versatile intermediates in synthetic chemistry. As such, great effort has been devoted to the cyclopropane construction. However, novel catalytic methods for cyclopropanation with two abundant substrates, mild conditions, high functional group tolerance, and broad scope are still highly desirable. Herein, we report an intermolecular electrocatalytic cyclopropanation of alkenyl trifluoroborates with methylene compounds. The reaction uses simple diphenyl sulfide as the electrocatalyst under base-free conditions. And thus, a broad scope of various methylene compounds as well as vinyltrifluoroborates is demonstrated, including styrenyl, 1,3-dienyl, fluorosulfonyl, and base-sensitive substrates. Preliminary mechanistic studies are presented, revealing the critical role of the boryl substituent to facilitate the desired pathway and the role of water as the hydrogen atom source.

Suggested Citation

  • Wei Yi & Peng-Cheng Xu & Tianyu He & Shuai Shi & Shenlin Huang, 2024. "Organoelectrocatalytic cyclopropanation of alkenyl trifluoroborates with methylene compounds," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-54082-8
    DOI: 10.1038/s41467-024-54082-8
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    References listed on IDEAS

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    1. Dylan E. Holst & Diana J. Wang & Min Ji Kim & Ilia A. Guzei & Zachary K. Wickens, 2021. "Aziridine synthesis by coupling amines and alkenes via an electrogenerated dication," Nature, Nature, vol. 596(7870), pages 74-79, August.
    2. Florian Berger & Matthew B. Plutschack & Julian Riegger & Wanwan Yu & Samira Speicher & Matthew Ho & Nils Frank & Tobias Ritter, 2019. "Site-selective and versatile aromatic C−H functionalization by thianthrenation," Nature, Nature, vol. 567(7747), pages 223-228, March.
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