Synthesis of C8-Aminated Pyrrolo-Phenanthridines or -Indoles via Series C(sp<sup>2</sup> or sp<sup>3</sup>)–H Activation and Fluorescence Study
Bo‐Sheng Zhang, Wan-Yuan Jia, Xue‐Ya Gou, Ying-Hui Yang, Fan Wang, Yiming Wang, Xi‐Cun Wang, Zheng‐Jun Quan
Abstract
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).