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α-Substituted vinyl azides: an emerging functionalized alkene
Chemical Society Reviews ( IF 46.2 ) Pub Date : 2017-11-10 00:00:00 , DOI: 10.1039/c7cs00017k
Junkai Fu 1, 2, 3, 4 , Giuseppe Zanoni 5, 6, 7, 8 , Edward A. Anderson 9, 10, 11, 12 , Xihe Bi 1, 2, 3, 4
Affiliation  

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.

中文翻译:

α-取代的乙烯基叠氮化物:一种新兴的官能化烯烃

乙烯基叠氮化物是高度通用的合成子,可提供与许多N-杂环和其他官能团的接触。α-取代的乙烯基叠氮化物(叠氮基亚乙烯基)是一类特殊的化合物,具有独特的反应性,不仅能够以叠氮化物的形式发生反应,而且还能够以自由基受体,烯胺型亲核试剂甚至亲电子试剂的形式发生反应,因此可提供范围广泛的含氮化合物化合物及其衍生物。乙烯基叠氮化物可以生成大量令人印象深刻的中间体,例如亚氨基二重氮离子,腈离子,亚氨基自由基和金属烯丙基自由基,并可以用于环加成,CH功能化,水解过程以及过渡金属/光氧化还原催化下的级联反应。除了提供合成协议以获取乙烯基叠氮化物外,
更新日期:2017-11-11
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