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Issue 23, 2017
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α-Substituted vinyl azides: an emerging functionalized alkene

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Abstract

Vinyl azides are highly versatile synthons that provide access to numerous N-heterocycles and other functional groups. α-Substituted vinyl azides (azido vinylidenes) are a special class that display unique reactivity, able to react not only as azides, but also as radical acceptors, enamine-type nucleophiles, and even electrophiles, thus delivering a wide range of nitrogen-containing compounds and their derivatives. An impressive variety of intermediates – such as iminodiazonium ions, nitrilium ions, iminyl radicals, and metal enaminyl radicals – can be generated from vinyl azides and exploited in cycloadditions, C–H functionalizations, hydrolysis processes, and cascade reactions under transition metal/photoredox catalysis. In addition to presenting synthetic protocols to access vinyl azides, this Review offers a comprehensive coverage of the development of their multifaceted reactivity, and highlights their potential as versatile precursors for synthetic applications.

Graphical abstract: α-Substituted vinyl azides: an emerging functionalized alkene

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Article information


Submitted
27 Sep 2017
First published
10 Nov 2017

Chem. Soc. Rev., 2017,46, 7208-7228
Article type
Review Article

α-Substituted vinyl azides: an emerging functionalized alkene

J. Fu, G. Zanoni, E. A. Anderson and X. Bi, Chem. Soc. Rev., 2017, 46, 7208
DOI: 10.1039/C7CS00017K

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