Vinyl azides in organic synthesis: an overview

Abstract

This review focuses on the application of vinyl azide in organic synthesis and highlights new strategies and methods using this compound to produce heterocycles and other organic compounds.

Visible light-assisted chemistry of vinyl azides and its applications in organic synthesis

“…There have been impressive efforts devoted to the manipulations of vinyl azides for the construction of cyclic and acyclic compounds. 2,7 This can be seen in a series of outstanding reviews dedicated to this area. Some of the notable ones are by Hu and DiMagno (2015), who discussed the synthesis of complex and diverse N-heterocyclic compounds from vinyl azides.…”

Copper-catalyzed crosscoupling of vinyl nitrenes and CF3-carbenes to synthesize CF3-2-azadienes

“…15 Despite these achievements, many of these reactions involve toxic substances, harsh reaction conditions, and high potential risk of explosion. 16 In our continuing interest in 2 H -azirine and isoxazole chemistry, 17 we envisioned that isoxazoles, as easily available and bench-stable heterocycles, could be used as vinyl nitrene precursors to react with α-CF 3 - N -tosylhydrazones through the tandem cleavage of N–O/C–N bonds and formation of a C–N double bond (Fig. 1B).…”

Nickel-Catalyzed Reaction between Vinyl Azides and an Alkyl Sulfonyl Radical Generated from DMSO: Rapid Access to β-Keto Sulfones

“…Vinyl azides as a crucial class of synthons have received extensive attention from organic chemists in chemical synthesis. − In this context, the addition reactions of vinyl azides with sulfonyl radicals are prominent, providing a reliable pathway to construct β-keto sulfones, enamines, phenanthridines, etc. (Scheme C). − Among them, β-keto sulfones are commonly employed as a critical synthetic building block in organic syntheses. − Notably, a series of reactions using sulfonyl hydrazines as the source of sulfonyl radicals to react with vinyl azides for the preparation of β-keto sulfones have been reported. ,,, In 2023, our group has developed a copper-catalyzed multicomponent cascade reaction for the synthesis of β-keto sulfones from vinyl azides, oxime esters, and Na 2 S 2 O 5 .…”