Three-Component Cascade Synthesis of Fully Substituted Trifluoromethyl Pyrroles via a Cu(II)/Rh(III)-Promoted Aza-Michael Addition/Trifluoromethylation Cyclization/Oxidation Reaction
Junying Ge, Qiuping Ding, Xinhua Wang, Yiyuan Peng
Abstract
A three-component cascade reaction of 1,3-enynes, anilines, and Togni-II reagent has been developed to give fully substituted trifluoromethyl pyrroles with high regioselectivity under mild conditions. The transformation proceeds through a Cu(II)/Rh(III)-promoted cascade aza-Michael addition/trifluoromethylation cyclization/oxidation reaction, affording trifluoromethyl pyrrole derivatives as primary products.
Topics & Concepts
TrifluoromethylationTrifluoromethylChemistryReagentRegioselectivityPyrroleCascadeMedicinal chemistryCascade reactionOrganic chemistryCombinatorial chemistryCatalysisChromatographyAlkylFluorine in Organic ChemistrySynthesis and Characterization of PyrrolesCyclopropane Reaction Mechanisms