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Allylic C–H oxygenation of unactivated internal olefins by the Cu/azodiformate catalyst system

Author

Listed:
  • Le Wang

    (Shanghai Jiao Tong University)

  • Yuan She

    (Shanghai Jiao Tong University)

  • Jie Xiao

    (Shanghai Jiao Tong University)

  • Zi-Hao Li

    (Shanghai Jiao Tong University)

  • Shen-Yuan Zhang

    (Shanghai Jiao Tong University)

  • Peng-Fei Lian

    (Shanghai Jiao Tong University)

  • Tong-Mei Ding

    (Shanghai Jiao Tong University)

  • Shu-Yu Zhang

    (Shanghai Jiao Tong University)

Abstract

Allylic ethers and alcohols are essential structural motifs commonly present in natural products and pharmaceuticals. Direct allylic C–H oxygenation of internal alkenes is one of the most direct methods, bypassing the necessity for an allylic leaving group that is needed in the traditional Tsuji–Trost reaction. Herein, we develop an efficient and practical method for synthesizing (E)-allyl ethers from readily available internal alkenes and alcohols or phenols via selective allylic C–H oxidation. Key advances include the use of a Cu/Azodiformate catalyst system to facilitate remote allylic C–H activation and the achievement of excellent chemoselectivity through a dynamic ligand exchange strategy using a bis(sulfonamide) ligand. This method features a broad substrate scope and functional group tolerance, successfully applied to the synthesis of various challenging medium-sized cyclic ethers (7-10 members) and large-ring lactones (14-20 members), with high regioselectivity and stereoselectivity.

Suggested Citation

  • Le Wang & Yuan She & Jie Xiao & Zi-Hao Li & Shen-Yuan Zhang & Peng-Fei Lian & Tong-Mei Ding & Shu-Yu Zhang, 2025. "Allylic C–H oxygenation of unactivated internal olefins by the Cu/azodiformate catalyst system," Nature Communications, Nature, vol. 16(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-56230-0
    DOI: 10.1038/s41467-025-56230-0
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