Synthesis of C8-Aminated Pyrrolo-Phenanthridines or -Indoles via Series C(sp² or sp³)–H Activation and Fluorescence Study

This report developed a method for the synthesis of C8-aminated pyrrolo-phenanthridines or -indoles by series ortho C­(sp²)–H amination/ipso C­(sp²)–H or C­(sp³)–H arylation. N-benzoyloxyamines, as electrophilic amination reagents, did not undergo an electrophilic substitution reaction with the pyrrole side, but they did undergo a site-selective C–H amination reaction with the benzene side via Pd/NBE catalysis. The C8-aminated pyrrolo-phenanthridines have strong fluorescence in solution and solid state. X-ray single crystal diffraction shows that the steric hindrance of amino and ortho benzene ring may inhibit aggregation-caused quenching (ACQ).