Cupric Halide‐Promoted Stereoselective Intramolecular Cis‐Addition to Construct (Z)‐Chloro(bromo)benzo[c, d]indoles. Issue 35 (15th September 2022)

• Record Type: Journal Article
• Authors: Diao, Hanying; Liu, Li; Wang, Jin; Lin, Yanfei; Zhao, Xiangyuan; Zeng, Heyang; Shi, Senlei; Gao, Wei; Yang, Long; Du, Guanben; Zhang, Lianpeng
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 35(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-09-15
• Subjects: AIE -- Alkynes -- Copper -- Heterocycles -- Stereoselective; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200811
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : 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.