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Peer-reviewedCC BY-NC-NDOrganic letters

Fluoroiodocarbene Addition to Bicyclobutanes: A Radical Handle for Quaternary Fluorinated Bicyclo[1.1.1]pentanes.

  • Arturs Sperga1
  • Toms Pfeifers1,2
  • Artis Kinens1,2
  • Janis Veliks1,3
  1. 1National Institute of Research and Innovation, Aizkraukles Street 21, LV-1006Riga, Latvia.
  2. 2Faculty of Medicine and Life Sciences, University of Latvia, Jelgavas Street 1, LV-1004Riga, Latvia.
  3. 3Faculty of Natural Sciences and Technology, Riga Technical University, Paula Valdena Street 3, LV-1048Riga, Latvia.
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Abstract

Fluorinated bicyclo[1.1.1]pentanes (F-BCPs) are valuable three-dimensional bioisosteres in drug discovery, yet methods for the direct construction of bridge-monofluorinated and quaternary F-BCPs remain scarce. Here, we report a fluoroiodocarbene addition to bicyclobutanes under mild conditions, providing 2-fluoro-2-iodobicyclo[1.1.1]pentanes. The C-I bond serves as a versatile radical handle, enabling synthesis of quaternary bridge-fluorinated BCPs, including Giese-type additions to activated alkenes and desulfonylative couplings. This strategy offers a practical, modular entry to bridge-fluorinated BCP architectures of potential interest for medicinal chemistry.

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Cite

BibTeXRIS
BibTeX
@article{sperga2026fluoroiodocarbene,
  title = {{Fluoroiodocarbene Addition to Bicyclobutanes: A Radical Handle for Quaternary Fluorinated Bicyclo[1.1.1]pentanes.}},
  author = {Arturs Sperga and Toms Pfeifers and Artis Kinens and Janis Veliks},
  journal = {Organic letters},
  year = {2026},
  month = sep,
  doi = {10.1021/acs.orglett.6c03112},
  url = {https://europepmc.org/article/MED/42918071},
  note = {CC BY-NC-ND},
}
RIS
TY  - JOUR
TI  - Fluoroiodocarbene Addition to Bicyclobutanes: A Radical Handle for Quaternary Fluorinated Bicyclo[1.1.1]pentanes.
AU  - Arturs Sperga
AU  - Toms Pfeifers
AU  - Artis Kinens
AU  - Janis Veliks
PY  - 2026
DA  - 2026/09/01
JO  - Organic letters
DO  - 10.1021/acs.orglett.6c03112
UR  - https://europepmc.org/article/MED/42918071
AB  - Fluorinated bicyclo[1.1.1]pentanes (F-BCPs) are valuable three-dimensional bioisosteres in drug discovery, yet methods for the direct construction of bridge-monofluorinated and quaternary F-BCPs remain scarce. Here, we report a fluoroiodocarbene addition to bicyclobutanes under mild conditions, providing 2-fluoro-2-iodobicyclo[1.1.1]pentanes. The C-I bond serves as a versatile radical handle, enabling synthesis of quaternary bridge-fluorinated BCPs, including Giese-type additions to activated alkenes and desulfonylative couplings. This strategy offers a practical, modular entry to bridge-fluorinated BCP architectures of potential interest for medicinal chemistry.
SN  - 1523-7060
SN  - 1523-7052
ER  -