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 generated 2-azirine to the diketone species, followed by intramolecular addition, N-C cleavage, and elimination.
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| http://dx.doi.org/10.1021/acs.orglett.1c02136 | DOI Listing |
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