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Green oxidation of indoles using halide catalysis

Author

Listed:
  • Jun Xu

    (Guizhou University of Traditional Chinese Medicine
    The Hong Kong University of Science and Technology(HKUST)
    Nanyang Technological University(NTU))

  • Lixin Liang

    (The Hong Kong University of Science and Technology(HKUST))

  • Haohao Zheng

    (Guizhou University of Traditional Chinese Medicine)

  • Yonggui Robin Chi

    (Nanyang Technological University(NTU))

  • Rongbiao Tong

    (The Hong Kong University of Science and Technology(HKUST))

Abstract

Oxidation of indoles is a fundamental organic transformation to deliver a variety of synthetically and pharmaceutically valuable nitrogen-containing compounds. Prior methods require the use of either organic oxidants (meta-chloroperoxybenzoic acid, N-bromosuccinimide, t-BuOCl) or stoichiometric toxic transition metals [Pb(OAc)4, OsO4, CrO3], which produced oxidant-derived by-products that are harmful to human health, pollute the environment and entail immediate purification. A general catalysis protocol using safer oxidants (H2O2, oxone, O2) is highly desirable. Herein, we report a unified, efficient halide catalysis for three oxidation reactions of indoles using oxone as the terminal oxidant, namely oxidative rearrangement of tetrahydro-β-carbolines, indole oxidation to 2-oxindoles, and Witkop oxidation. This halide catalysis protocol represents a general, green oxidation method and is expected to be used widely due to several advantageous aspects including waste prevention, less hazardous chemical synthesis, and sustainable halide catalysis.

Suggested Citation

  • Jun Xu & Lixin Liang & Haohao Zheng & Yonggui Robin Chi & Rongbiao Tong, 2019. "Green oxidation of indoles using halide catalysis," Nature Communications, Nature, vol. 10(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-12768-4
    DOI: 10.1038/s41467-019-12768-4
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