A range of densely functionalized ullazines have been synthesized by a one-pot Rh(III)-catalyzed twofold C−H activation/oxidative annulation of N-arylpyrroles with alkynes. Electrophilic bromination at 5- or 5,7- positions of the EWG-substituted ullazine core offers an interesting single or double entry for further extended functionalization. Mechanistic considerations suggest two complementary paths, EWG-assisted and SEAr, for the C−H activations. All ullazines exhibit strong fluorescence emissions. Ullazines bearing thiophene and triarylamine units at 5- and 5,7- positions show a significant bathochromic shift in their emission spectra, attributed to the more extended electronic circuits present.
CITATION STYLE
Otero-Riesgo, S., Varela, J. A., & Saá, C. (2024). One-Pot Rh(III)-Catalyzed Twofold C−H Activation/Oxidative Annulation of N-Arylpyrroles with Alkynes to Fluorescent Ullazines. Advanced Synthesis and Catalysis. https://doi.org/10.1002/adsc.202400043
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