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Copper‐Catalyzed Cascade Cyclization Reaction of 2‐Haloaryltriazenes and Sodium Azide: Selective Synthesis of 2 H ‐Benzotriazoles in Water
Author(s) -
Shang Xiaobo,
Zhao Shixian,
Chen Wanzhi,
Chen Chao,
Qiu Huayu
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303712
Subject(s) - nitrene , sodium azide , chemistry , catalysis , azide , intramolecular force , combinatorial chemistry , aryl , copper , cascade , sodium , medicinal chemistry , organic chemistry , alkyl , chromatography
Abstract A new approach to the synthesis of 2 H ‐benzotriazoles is described. This strategy is based on the copper‐catalyzed CN coupling of 2‐haloaryltriazenes or 2‐haloazo compounds with sodium azide and the intramolecular addition of nitrene to NN bonds. This approach allows the synthesis of various N ‐amino‐ and N ‐aryl‐2 H ‐benzotriazoles in water, in good to excellent yields. The procedure is simple and the starting materials and catalyst are easily available, offering a practical and convenient synthetic route to 2‐substituted benzotriazoles.