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Nucleophilic aromatization of monoterpenes from isoprene under nickel/iodine cascade catalysis

Author

Listed:
  • Wei-Song Zhang

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

  • Ding-Wei Ji

    (Chinese Academy of Sciences)

  • Yang Yang

    (Chinese Academy of Sciences)

  • Ting-Ting Song

    (Chinese Academy of Sciences)

  • Gong Zhang

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

  • Xiao-Yu Wang

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

  • Qing-An Chen

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

Abstract

As a large number of organic compounds possessing two isoprene units, monoterpenes and monoterpenoids play important roles in pharmaceutical, cosmetic, agricultural, and food industries. In nature, monoterpenes are constructed from geranyl pyrophosphate (C10) via various transformations. Herein, the bulk C5 chemical—isoprene, is used for the creation of various monoterpenoids via a nucleophilic aromatization of monoterpenes under cascade catalysis of nickel and iodine. Drugs and oil mixtures from conifer and lemon can be convergently transformed to the desired monoterpenoid. Preliminary mechanistic studies are conducted to get insights about reaction pathway. Two types of cyclic monoterpenes can be respectively introduced onto two similar heterocycles via orthogonal C–H functionalization. And various hybrid terpenyl indoles are programmatically assembled from abundant C5 or C10 blocks. This work not only contributes a high chemo-, regio-, and redox-selective transformation of isoprene, but also provides a complementary approach for the creation of unnatural monoterpenoids.

Suggested Citation

  • Wei-Song Zhang & Ding-Wei Ji & Yang Yang & Ting-Ting Song & Gong Zhang & Xiao-Yu Wang & Qing-An Chen, 2023. "Nucleophilic aromatization of monoterpenes from isoprene under nickel/iodine cascade catalysis," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-42847-6
    DOI: 10.1038/s41467-023-42847-6
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