Silver-Catalyzed Regioselective Synthesis of Highly Substituted 2-Trifluoromethyl Pyrroles
Wei Wu1, Shunli Wen2, Xinyu Zhang2
1Fujian Engineering Research Center of New Chinese lacquer Material, Ocean College, Minjiang University, Fuzhou, 350108, China.
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.
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