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0 202606029 - 202606029

DOI: https://doi.org/10.6023/cjoc202606029

REVIEW

Advances in Asymmetric Synthesis of Chiral Organofluorine Compounds via Hypervalent Iodine Catalysis

  • Zhong Shengyu ,
  • Shi Lei
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  • aSchool of Science, Harbin Institute of Technology (Shenzhen), Shenzhen 518055

Received date: 2026-06-24

  Revised date: 2026-08-19

  Online published: 2026-09-16

Supported by

National Natural Science Foundation of China (No. 22271069), the Shenzhen Medical Research Fund (No. D2501008), and the Shenzhen Science and Technology Program (Nos. JCYJ20240813105110014 and GXWD20231130100539001).

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Abstract

Organofluorine compounds are widely applied in pharmaceuticals and agrochemicals, yet naturally occurring organic fluorides are extremely rare. Notably, the construction of carbon-fluorine bonds poses considerable challenges. Hypervalent iodine(III) catalysis offers a distinct approach to the asymmetric synthesis of chiral organofluorine compounds under mild conditions by reversing the polarity of inexpensive nucleophilic fluoride sources to generate electrophilic hypervalent iodine(III) fluoride species. This Review systematically summarizes the progress in hypervalent iodine(III)-catalyzed asymmetric synthesis of chiral organofluorine compounds from 2014 to the present, covering the construction of chiral monofluorinated, difluorinated, and polyfluorinated molecules. Representative transformations discussed include carbonyl α-fluorination, olefin fluorocyclization, fluorinative dearomatization of phenols, fluorination of allenes, 1,2-difluorination, gem-difluorination, 1,3-difluorination, and fluorination of CF3-substituted alkenes. Key aspects of the reported systems, including catalyst design, enantioselectivity control and catalytic mechanisms, are discussed. Finally, current challenges and future directions are highlighted.

Key words： hypervalent iodine(III); asymmetric catalysis; nucleophilic fluorination; chiral organofluorine compounds; umpolung

Cite this article

Zhong Shengyu , Shi Lei . Advances in Asymmetric Synthesis of Chiral Organofluorine Compounds via Hypervalent Iodine Catalysis[J]. Chinese Journal of Organic Chemistry, 0 : 202606029 -202606029 . DOI: 10.6023/cjoc202606029

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