Tetrafluoroethylene-containing azides are accessed in two steps (one pot) from tetrafluoroalkyl bromides by metalation and reaction with electrophilic azides. Subsequent copper(i)-catalyzed azide-alkyne cycloaddition afforded N-tetrafluoroethyl and N-tetrafluoroethylene 4-substituted 1,2,3-triazoles. In addition, the protocol for the synthesis of 4,5-disubstituted 1,2,3-triazoles is presented.
The first one-pot synthesis of N-substituted 2-H-4-benzylidene imidazolones and their subsequent palladium-catalyzed and copper-assisted direct C2-H arylation and alkenylation with aryl- and alkenylhalides are described. This innovative synthesis is step-economical, azide-free, high yielding, highly flexible in the introduction of a variety of electronically different groups, and can be operated on large-scale. Moreover, the method allows direct access to C2-arylated or alkenylated imidazolone-based green fluorescent protein (GFP) and Kaede protein fluorophores, including ortho-hydroxylated models.
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