Silver-Catalyzed Tandem Hydroazidation/Alkyne-Azide Cycloaddition of Diynes with TMS-N3: An Easy Access to 1,5-Fused 1,2,3-Triazole Frameworks

Org Lett. 2015 May 1;17(9):2198-201. doi: 10.1021/acs.orglett.5b00784. Epub 2015 Apr 20.

Abstract

A general cascade hydroazidation and alkyne-azide 1,3-dipolar cycloaddition of diynes using silver catalysis is reported. A wide variety of diynes participated in the reaction with trimethylsilyl azide (TMS-N3) in the presence of H2O, affording the corresponding 1,5-fused-1,2,3-triazoles in good-to-excellent yields. This unprecedented protocol is operationally simple with a broad substrate scope, good functional group tolerance, and high reaction efficiency, thus providing easy access to various fused 1,2,3-triazoles.