Regioselective rapid synthesis of fully substituted 1,2,3-triazoles mediated by propargyl cations

Org Lett. 2013 Oct 18;15(20):5222-5. doi: 10.1021/ol402387w. Epub 2013 Oct 2.

Abstract

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.