Hypervalent Iodine‐Mediated Azidation Reactions
Hypervalent Iodine‐Mediated Azidation Reactions
复制标题
高价碘介导的叠氮化反应
DOI：
10.1002/ejoc.202200754
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发表时间：
2022
影响因子：
2.8
通讯作者：
Yusubov, Mekhman S.
中科院分区：
文献类型：
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作者：
Mironova, Irina A.;Kirsch, Stefan F.;Zhdankin, Viktor V.;Yoshimura, Akira;Yusubov, Mekhman S.
有机叠氮化合物在科学技术的各个领域有着广泛的应用。本文综述了近年来利用高价碘试剂直接一步合成多种有机叠氮化合物的研究进展。综述的第一部分讨论了由常见的高价碘试剂(如二乙酰氧基碘苯或碘代苯)和叠氮阴离子的来源(TMN3或NaN3)在 中生成的不稳定叠氮碘的叠氮化反应。第二部分综述了稳定的叠氮苯并氧杂多酚作为有用的叠氮试剂的应用，这些试剂可以在温和的反应条件下选择性地直接进行C-−H键或双碳-碳键的叠氮化反应。叠氮苯并恶酚的使用消除了传统方法的主要缺点，如需要对有机底物进行预官能化和苛刻的反应条件。叠氮苯并氧杂环己烷的合成应用使得在合成后期对包括复杂分子在内的大量有机底物进行直接选择性叠氮化成为可能。
Organic azides have found wide application in various fields of science and technology. This review summarizes recently developed approaches to the direct, one‐step synthesis of diverse organic azides utilizing hypervalent iodine reagents. The first part of review deals with the azidation using unstable azidoiodinanes generatedin situfrom common hypervalent iodine reagents (such as diacetoxyiodobenzene or iodosylbenzene) and a source of azide anion (TMSN3or NaN3). The second part of review is dedicated to the application of stable azidobenziodoxoles as useful azidating reagents that allow selective direct azidation of C−H bonds or double carbon‐carbon bonds under mild reaction conditions. The use of azidobenziodoxoles eliminates the main disadvantages of the traditional approaches to organic azides, such as the need in pre‐functionalization of organic substrates and harsh reaction conditions. Synthetic application of azidobenziodoxoles made possible direct selective azidation of a plethora of organic substrates including complex molecules at the late synthetic stage.