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

• Published in: European journal of organic chemistry 2022-09, Vol.2022 (35), p.n/a
• Main Authors: Diao, Hanying, Liu, Li, Wang, Jin, Lin, Yanfei, Zhao, Xiangyuan, Zeng, Heyang, Shi, Senlei, Gao, Wei, Yang, Long, Du, Guanben, Zhang, Lianpeng
• Format: Article
• Language: English
• Subjects: AIE; Alkynes; Copper; Heterocycles; Stereoselective
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202200811

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. In this paper, we have developed tunable copper‐promoted stereoselective intramolecular cis‐addition annulation reactions for controllable synthesis of (Z)‐chloro(bromo)benzo[c,d]indoles under mild conditions. A novel fluorescent molecule with AIE properties was constructed by Suzuki coupling reaction using (Z)‐bromobenzo[c,d]indole 3 b as the starting material, and its optical properties was investigated.