Regioselective Rapid Synthesis of Fully-substituted 1,2,3-Triazoles Mediated by Propargyl Cations

Regioselective Rapid Synthesis of Fully-substituted 1,2,3-Triazoles Mediated by Propargyl Cations
Huan Zhang, Hiroki Tanimoto, Tsumoru Morimoto, Yasuhiro Nishiyama, Kiyomi Kakiuchi
Org. Lett. 2013, 15, 5222-5225.

http://pubs.acs.org/doi/abs/10.1021/ol402387w

Regioselective rapid triazole syntheses at low temperature are described. Organic azides and propargyl cations generated by acids gave fully substituted 1H-1,2,3-triazoles. Most reactions could be performed in 5 min at not only rt but also −90 °C. Both terminal and internal alkynes were acceptable, and the sterically bulky substituents could afford the products smoothly. Various types of three-component coupling reactions were demonstrated, and the presence of allenylaminodiazonium intermediates was indicated.

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