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

Abstract

A convenient and efficient method for one pot synthesis of polysubstituted (Z)-halobenzo [c,d]indoles from 8-alkynyl-1naphthylamine derivatives using CuCl 2 and CuBr 2 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.

Copper-catalyzed construction of (Z)-benzo[cd]indoles: stereoselective intramolecular trans-addition and SN–Ar reaction

“…The construction of naphthalene-fused heterocycles based on the controllable functionalization of alkynes has always been one of the main research interests in our group (Scheme 2c). 10 On the other hand, as a cheap metal, copper shows a broad spectrum of catalytic activity in heterocycle synthesis. 11 Moreover, aromatic nucleophilic substitution is one of the most basic and widely used reactions for the functionalization of aromatic organic compounds.…”