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

Ruitong Zhang, Shengqi Zhou, Yijing Li, Yaxing Wu, Xiangyu Chen, Fei Wang, Yunchen Jiang, Xingwei Guo () and Chao Chen ()
Additional contact information
Ruitong Zhang: Haidian
Shengqi Zhou: Haidian
Yijing Li: Haidian
Yaxing Wu: Haidian
Xiangyu Chen: Haidian
Fei Wang: Haidian
Yunchen Jiang: Haidian
Xingwei Guo: Haidian
Chao Chen: Haidian

Nature Communications, 2025, vol. 16, issue 1, 1-10

Abstract: 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.

Date: 2025
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DOI: 10.1038/s41467-025-59772-5

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