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Selective radical-type perfluoro-tert-butylation of unsaturated compounds with a stable and scalable reagent

Author

Listed:
  • Ruitong Zhang

    (Haidian)

  • Shengqi Zhou

    (Haidian)

  • Yijing Li

    (Haidian)

  • Yaxing Wu

    (Haidian)

  • Xiangyu Chen

    (Haidian)

  • Fei Wang

    (Haidian)

  • Yunchen Jiang

    (Haidian)

  • Xingwei Guo

    (Haidian
    Southern University of Science and Technology)

  • Chao Chen

    (Haidian)

Abstract

Despite the promising potential of the perfluoro-tert-butyl group in diverse fields such as magnetic resonance imaging, material science and drug design, incorporating this group into organic molecules is still a formidable task, primarily due to its bulky structure and unique fluorine effect. Herein, we describe a stable and scalable reagent for radical-type perfluoro-tert-butylation, which is synthesized in large scale from commercial perfluoro-tert-butanol and a designed benzothiazole hypervalent iodonium salt. Highly E-selective photo-driven C(sp2)–H functionalization of styrene derivatives is achieved in a triplet-triplet energy transfer halted manner, while thermally disfavored Z-products are also accessible by removing the energy antagonist. The application of this method is further demonstrated by late-stage functionalization and divergent synthesis of perfluoro-tert-butylated compounds.

Suggested Citation

  • Ruitong Zhang & Shengqi Zhou & Yijing Li & Yaxing Wu & Xiangyu Chen & Fei Wang & Yunchen Jiang & Xingwei Guo & Chao Chen, 2025. "Selective radical-type perfluoro-tert-butylation of unsaturated compounds with a stable and scalable reagent," Nature Communications, Nature, vol. 16(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-59772-5
    DOI: 10.1038/s41467-025-59772-5
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