Cupric Halide-Promoted Stereoselective Intramolecular Cis-Addition to Construct (Z)-Chloro(bromo)benzo[c,d]indoles

A convenient and efficient method for one pot synthesis of polysubstituted (Z)-halobenzo[c,d]indoles from 8-alkynyl-1-naphthylamine derivatives using CuCl2 and CuBr2 as the halogenated reagents has been developed. In this protocol, both (Z)-chloro and bromobenzo[c,d] indole derivatives can be obtained in moderate to good yields by copper halide-promoted stereoselective intramolecular cis-addition annulation reactions. A novel fluorescent molecule with AIE properties was constructed via Suzuki coupling reaction and its optical properties was investigated, which made them possible candidates for optoelectronic conjugated materials.

Automated summary

A convenient and efficient one pot synthesis method for polysubstituted (Z)-halobenzo[c,d]indoles has been developed using CuCl2 and CuBr2 as halogenated reagents. The protocol allows for the synthesis of both (Z)-chloro and bromobenzo[c,d]indole derivatives in moderate to good yields using copper halide-promoted intramolecular cis-addition annulation reactions. A novel fluorescent molecule with aggregation-induced emission (AIE) properties was constructed via Suzuki coupling reaction, and its optical properties were investigated, showing potential applications as optoelectronic conjugated materials.