Metal-Free CN- and NN-Bond Formation: Synthesis of 1,2,3-Triazoles from Ketones, N-Tosylhydrazines, and Amines in One Pot

• Published in: Chemistry : a European journal 2014-12, Vol.20 (52), p.17635-17639
• Main Authors: Chen, Zhengkai, Yan, Qiangqiang, Liu, Zhanxiang, Zhang , Yuhong
• Format: Article
• Language: English
• Subjects: 1,2,3‐triazoles; 3-triazoles; Amines; Amines - chemistry; Aniline; anilines; Catalysis; Formations; Iodine; Ketones; Ketones - chemistry; metal-free reactions; Metals; Molecular Structure; Synthesis; synthetic methods; Tosyl Compounds - chemistry; Triazoles - chemical synthesis; Triazoles - chemistry
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201405057

A novel synthetic approach toward 1,4‐disubstituted 1,2,3‐triazoles by CN‐ and NN‐bond formation has been established under transition‐metal‐free conditions. Complete control of the regioselectivity was successfully achieved. Commercially available anilines, ketones, and N‐tosylhydrazine were treated with molecular iodine in one pot to allow the regioselective generation of 1,4‐disubstituted 1,2,3‐triazoles in high yields without the use of azides. A novel synthetic approach toward 1,4‐disubstituted 1,2,3‐triazoles by CN‐ and NN‐bond formation has been established under transition‐metal‐free conditions (see scheme). Complete control of regioselectivity was successfully achieved and anilines, ketones, and N‐tosylhydrazines were treated with molecular iodine in one pot to allow the formation of 1,4‐disubstitued 1,2,3‐triazoles in high yields without the use of azides.