Copper-Catalyzed Ring-Opening 1,3-Aminotrifluoromethylation of Arylcyclopropanes
Huan Zhang, Haiwen Xiao, Feng Jiang, Yewen Fang, Lin Zhu, Chaozhong Li
Abstract
The copper-catalyzed reaction of arylcyclopropanes, N-fluorobis(arenesulfonyl)imides, and (bpy)Zn(CF3)2 (bpy = 2,2′-bipyridine) at room temperature affords the corresponding ring-opening 1,3-aminotrifluoromethylation products in satisfactory yields. The protocol is highly regioselective, providing a convenient entry to γ-trifluoromethylated amines. A mechanism involving the trifluoromethylation of benzyl radicals is proposed.
Topics & Concepts
TrifluoromethylationChemistryRegioselectivityCatalysisRing (chemistry)CopperRadicalMedicinal chemistryCombinatorial chemistryBipyridineOrganic chemistryTrifluoromethylCrystal structureAlkylFluorine in Organic ChemistryCyclopropane Reaction Mechanisms