1447966-72-4Relevant academic research and scientific papers
Rh(iii)-Catalyzed regioselective mono- and di-iodination of azobenzenes using alkyl iodide
Li, Jixing,Cong, Wenxia,Gao, Zeng,Zhang, Jinlong,Yang, Huameng,Jiang, Gaoxi
, p. 3479 - 3486 (2018/05/23)
A new approach for highly regioselective iodination of azobenzenes with alkyl iodide as the iodinating reagent enabled by Rh-catalyzed oxidative C-H activation has been developed. By changing the oxidant, various mono- and di-iodinated azobenzenes were smoothly obtained in moderate to excellent yields, respectively. The preliminary mechanistic study reveals that the reaction process might undergo electrophilic substitution of the directed ortho metalated five-membered rhodacycle compound by an iodine cationic species generated in situ from alkyl iodide and oxidant.
Palladium-catalyzed regioselective halogenation of aromatic azo compounds
Maa, Xian-Tao,Tian, Shi-Kai
supporting information, p. 337 - 340 (2013/05/08)
A highly regioselective halogenation reaction of symmetrical and unsymmetrical aromatic azo compounds has been developed at room temperature or at 50 °C. In the presence of 5 mol% palladium diacetate and 0.5 equiv. of p-toluenesulfonic acid, a range of symmetrical aromatic azo compounds smoothly undergo monobromination with N-bromosuccinimide to give the corresponding unsymmetrical aromatic azo compounds in good to excellent yields with >99:1 ortho-selectivity. This chemistry has been successfully extended to unsymmetrical aromatic azo compounds, whose electronricher aryl groups prefer to be monobrominated. Moreover, replacing N-bromosuccinimide with Niodosuccinimide in the reaction allows the synthesis of monoiodinated aromatic azo compounds with >99:1 regioselectivity.
