Abstract:
Modification of benzotriazoles with iodonium salts [diphenyl- and (E)-styrylphenyliodonium tosylates] occurs at the N1-position in the presence of K2CO3 as a base and CuI as a catalyst in CH2Cl2, whereas in the presence of stoichiometric amount of [Cu2(TMEDA)2(OH)2]Cl2 complex regioselective N2-modification proceeds. Two new CuI complexes based on benzotriazoles were synthesized and their crystal structures were determined by X-ray powder diffraction analysis.
Document Type:
Article
Language: English
Citation:
D. V. Davydov, V. V. Chernyshev, V. B. Rybakov, Yu. F. Oprunenko, I. P. Beletskaya, “Regioselective N1- or N2-modification of benzotriazoles with iodonium salts in the presence of copper compounds”, Mendeleev Commun., 28:3 (2018), 287–289
Linking options:
https://www.mathnet.ru/eng/mendc1740
https://www.mathnet.ru/eng/mendc/v28/i3/p287
This publication is cited in the following 6 articles:
Quanyun Liu, Haoke Chu, Junju Mai, Haobing Yang, Mei-Hua Shen, Hua-Dong Xu, “Molybdenum-catalyzed deoxygenative heterocyclization of 2-nitroazobenzenes: a novel strategy for catalytic synthesis of 2-aryl-2H-benzo[d][1,2,3]triazoles”, Org. Biomol. Chem., 22:5 (2024), 954
Dachao Wang, Xiaoting Gan, Lewei Zhou, Hanyu Shu, Jun Zhou, “Synthesis of functionized N-arylbenzotriazoles via palladium catalyzed intramolecular amination”, Tetrahedron Letters, 88 (2022), 153587
Alexandra Pacheco-Benichou, Thierry Besson, Corinne Fruit, “Diaryliodoniums Salts as Coupling Partners for Transition-Metal Catalyzed C- and N-Arylation of Heteroarenes”, Catalysts, 10:5 (2020), 483
Alexei D. Averin, Anton S. Abel, Olga K. Grigorova, Gennadij V. Latyshev, Yury N. Kotovshchikov, Alexander Yu. Mitrofanov, Alla Bessmertnykh-Lemeune, Irina P. Beletskaya, “Recent achievements in copper catalysis for C–N bond formation”, Pure and Applied Chemistry, 92:8 (2020), 1181
Tom Wirtanen, Eduardo Rodrigo, Siegfried R. Waldvogel, “Selective and Scalable Electrosynthesis of 2H‐2‐(Aryl)‐benzo[d]‐1,2,3‐triazoles and Their N‐Oxides by Using Leaded Bronze Cathodes”, Chemistry A European J, 26:25 (2020), 5592
D. V. Davydov, P. K. Sazonov, Yu. F. Oprunenko, “Regioselectivity of the Chan–Lam coupling of ambident nitropyrazoles with trans-styrylboronic acid”, Mendeleev Commun., 30:2 (2020), 185–187
Contact us: