General and Scalable Approach to Trifluoromethyl-Substituted Cyclopropanes
Volodymyr Ahunovych, Anton A. Klipkov, Maksym Ya. Bugera, Karen V. Tarasenko, Serhii Trofymchuk, Oleh Stanko, Andrii Boretskyi, Mykola Zheludenko, Iryna V. Sadkova, Pavel K. Mykhailiuk
Abstract
CF 3 -cyclopropanes with aliphatic, aromatic, and even heteroaromatic substituents were prepared on a multigram scale by deoxyfluorination of cyclopropane carboxylic acids or their salts with sulfur tetrafluoride. For labile α-pyridine acetic acids, only the use of their potassium salts allowed to obtain the needed products. Derivatization of CF 3 -cyclopropanes into building blocks ready for direct use in medicinal chemistry was performed.
Topics & Concepts
CyclopropaneChemistryDerivatizationOrganic chemistryPyridineTrifluoromethylAcetic acidSulfurRing (chemistry)AlkylHigh-performance liquid chromatographyFluorine in Organic ChemistryCyclopropane Reaction MechanismsSynthesis and Biological Evaluation