1916-72-9Relevant articles and documents
Cu(I)/KOH-Promoted Condensation between o-Arylenediamines and Nitroarenes to Access 2-Aryl-2H-Benzotriazoles
Li, Hong-Chen,Gao, Wen-Xia,Huang, Xiao-Bo,Zhou, Yun-Bing,Liu, Miao-Chang,Wu, Hua-Yue
, p. 2847 - 2851 (2020/06/02)
Reported is the condensation between o-arylenediamines and nitroarenes enabled by a cooperative action of acid and base, providing a direct entry to 2-aryl-2H-benzotriazoles. The potential practicability of this methodology was demonstrated by 100 mmol-scale reactions and the synthesis of serotonin/dopamine receptor ligand and human growth hormone. (Figure presented.).
Selective Synthesis of N-H and N-Aryl Benzotriazoles by the [3 + 2] Annulation of Sodium Azide with Arynes
Guin, Avishek,Gaykar, Rahul N.,Bhattacharjee, Subrata,Biju, Akkattu T.
, p. 12692 - 12699 (2019/10/11)
The synthetic utility of NaN3 as the azide component in the [3 + 2] annulation with arynes generated from 2-(trimethylsilyl)aryltriflates resulting in the transition-metal-free synthesis of N-H and N-aryl benzotriazoles has been demonstrated. Using CsF as the fluoride source in CH3CN, the N-H benzotriazoles are formed in high selectivity instead of the expected azidobenzene. Interestingly, N-aryl benzotriazoles are formed using KF and THF as solvent in an open-flask reaction. Moreover, a method for the N1-arylation of benzotriazole is also presented.
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.