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<p>Despite the promising potential of the perfluoro-<i>tert</i>-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-<i>tert</i>-butylation, which is synthesized in large scale from commercial perfluoro-<i>tert</i>-butanol and a designed benzothiazole hypervalent iodonium salt. Highly <i>E</i>-selective photo-driven C(sp<sup>2</sup>)–H functionalization of styrene derivatives is achieved in a triplet-triplet energy transfer halted manner, while thermally disfavored <i>Z</i>-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-<i>tert</i>-butylated compounds.</p>

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

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年5月14日

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  • Ruitong Zhang,
  • Shengqi Zhou,
  • Yijing Li,
  • Yaxing Wu,
  • Xiangyu Chen,
  • Fei Wang,
  • Yunchen Jiang,
  • Xingwei Guo,
  • Chao Chen

摘要

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.