One-Pot Synthesis of Highly Substituted Polyheteroaromatic Compounds by Rhodium(III)-Catalyzed Multiple CH Activation and Annulation

A new method for the synthesis of highly substituted naphthyridine‐based polyheteroaromatic compounds in high yields proceeds through rhodium(III)‐catalyzed multiple CH bond cleavage and CC and CN bond formation in a one‐pot process. Such highly substituted polyheteroaromatic compounds have attracted much attention because of their unique π‐conjugation, which make them suitable materials for organic semiconductors and luminescent materials. Furthermore, a possible mechanism, which involves multiple chelation‐assisted ortho CH activation, alkyne insertion, and reductive elimination, is proposed for this transformation. Activated and annulated: A rhodium‐catalyzed one‐pot synthesis of highly substituted polyheteroaromatic compounds from N‐hydroxybenzamidines and alkynes is described. This reaction likely proceeds through multiple CH bond activation and annulation.