Metal-Free TFA-Promoted Regioselective (Hetero)Arylation: Synthesis of (Hetero)Aryl Substituted and Carbazole/Oxepine Fused N-Heterocycles

Metal-free TFA promoted arylation/heteroarylation was achieved under mild conditions via the reaction of chloro-derivatives of nitrogen heterocycles [e. g., =C-C(Cl)=N-] with electron rich arenes/heteroarenes. It was also observed that apart from participating in the heteroarylation step, TFA was able to facilitate the hydroarylation/o-arylation process in the same pot affording the carbazole/oxepine fused N-heterocycles. The reaction proceeded with similar efficiency on gram scale.

Automated summary

Metal-free TFA promoted arylation/heteroarylation was achieved under mild conditions via the reaction of chloro-derivatives of nitrogen heterocycles with electron rich arenes/heteroarenes. It was also observed that TFA was able to facilitate other reactions, resulting in the formation of fused N-heterocycles.