Silver-Catalyzed Regioselective Synthesis of Highly Substituted 2-Trifluoromethyl Pyrroles
Wei Wu, Shunli Wen, Xinyu Zhang, Qi Lin, Zhiqiang Weng
Abstract
An efficient and regioselective synthesis of highly substituted 2-trifluoromethyl pyrrole derivatives via silver-catalyzed cyclization of vinyl azides with ethyl 4,4,4-trifluoro-3-oxobutanoate is reported. Various α-(heteo)aryl, alkyl, β-aryl, as well as α,β-disubstituted vinyl azides, participate in this transformation. The reaction mechanism likely involves the addition of in situ generated 2H-azirine to the diketone species, followed by intramolecular addition, N–C1 cleavage, and elimination.
Topics & Concepts
ChemistryRegioselectivityTrifluoromethylArylCatalysisIntramolecular forceCleavage (geology)Medicinal chemistryAlkylPyrroleCombinatorial chemistryOrganic chemistryEngineeringFracture (geology)Geotechnical engineeringFluorine in Organic ChemistryCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions