Chemical synthesis study reports fluoroiodocarbene addition to bicyclobutanes, highlighting a modular route to quaternary bridge-fluorinated bioisosteres for medicinal chemistry.
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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Sperga et al. (2026) studied this question.
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