Novel Entry to Fluorinated Cyclopropanes
Nickel-Catalyzed Cross-Electrophile Coupling of the Difluoromethyl Group for Fluorinated Cyclopropane Synthesis: E. L. Lucas, T. M. McGinnis, A. J. Castro, E. R. Jarvo
Synlett 2021, 32, DOI: 10.1055/s-0040-1706013
Fluorinated cyclopropanes are structural units that merge two of the most distinctive elements used in medicinal chemistry to modify and tune the pharmacological properties of bioactive compounds: fluorine atoms and cyclopropyl rings. It is therefore not surprising that the medicinal and synthetic chemistry communities look with particular interest at novel methods for accessing fluorocyclopropanes, especially in a stereocontrolled manner. A conceptually new synthesis of the title compounds has been recently described by the group of Professor Elizabeth R. Jarvo from the University of California, Irvine (USA). The method relies on a photocatalytic olefin difluoromethylation coupled with a Ni-catalyzed intramolecular cross-electrophile coupling reaction between a CF2H group and a benzylic ether.
Professor Jarvo said: “This method provides a new and convenient strategy for the synthesis of the target fluorinated cyclopropane motif.”