General silver-catalyzed hydroazidation of terminal alkynes by combining TMS-N3 and H2O: synthesis of vinyl azides

Org Lett. 2014 Jul 18;16(14):3668-71. doi: 10.1021/ol501661k. Epub 2014 Jun 27.

Abstract

A general hydroazidation of unactivated alkynes using silver catalysis is reported. The reactions of diverse terminal alkynes with trimethylsilyl azide (TMS-N(3)) in the presence of H(2)O afforded the corresponding vinyl azides in good to excellent yields. This reaction has a broad substrate scope, good functional group tolerance, simple operation, and high reaction efficiency, thus providing an easy access to various functionalized vinyl azides.