α-Substituted vinyl azides: an emerging functionalized alkene

Journal article

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.

Authors: Fu, J; Zanoni, G; Anderson, EA; Bi, X

• Publication status: Published
• Peer review status: Peer reviewed
• Publisher: Royal Society of Chemistry
• Journal: Chemical Society Reviews
• Volume: 46
• Issue: 23
• Pages: 7208-7228
• Publication date: 2017-11-10
• Acceptance date: 2017-10-25
• DOI: 10.1039/c7cs00017k
• EISSN: 1460-4744
• ISSN: 0306-0012
• Pmid: 29125611
• Language: English