Silver-Mediated [3 + 2] Cycloaddition of Azomethine Ylides with Trifluoroacetimidoyl Chlorides for the Synthesis of 5-(Trifluoromethyl)imidazoles
Hefei Yang, Shu‐Ning Lu, Zhengkai Chen, Xiao‐Feng Wu
Abstract
A silver-mediated [3 + 2] cycloaddition of azomethine ylides with trifluoroacetimidoyl chlorides for the rapid assembly of 5-(trifluoromethyl)imidazoles has been developed. Notable features of the reaction include readily accessible reagents, a broad substrate scope, and high efficiency. The protocol can be successfully applied to construct the analogue of the specific allosteric modulator of GABAA receptors. The silver species could be recycled by a simple operation.
Topics & Concepts
ChemistryCycloadditionReagentTrifluoromethylSubstrate (aquarium)Combinatorial chemistryAzomethine ylideOrganic chemistry1,3-Dipolar cycloadditionCatalysisGeologyAlkylOceanographyFluorine in Organic ChemistryCyclopropane Reaction MechanismsClick Chemistry and Applications