Recent Advances in the Synthesis of Aryl Nitrile Compounds,Advanced Synthesis & Catalysis

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Recent Advances in the Synthesis of Aryl Nitrile Compounds
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-12-04 , DOI: 10.1002/adsc.201700875
Guobing Yan ₁ , Yan Zhang ₂ , Jianbo Wang ₂

Affiliation

Aryl nitriles are widely found in natural products, pharmaceuticals, agrochemicals, dyes, and herbicides. Moreover, because the cyano group can be easily converted into various functional groups, aryl nitriles are important intermediates in synthetic organic chemistry. Consequently, the development of new methodologies for the synthesis of aryl nitriles is of significant interest. The traditional methods for their synthesis include Sandmeyer reactions, Rosenmund–von Braun reactions, as well as dehydration reactions of aldoximes and amides. In recent years, numerous efforts have been devoted to transition metal‐catalyzed cyanation reactions of aryl (pseudo)halides, organometallic reagents and aryl C–H bonds. A number of cyanating reagents have been explored for such transformations, including metal cyanides and organic cyano group sources. In addition, styrenes and aryl‐substituted alkynes are successfully converted into aryl nitriles through carbon‐carbon double or triple bond cleavage. Various benzylic compounds have also been used for the synthesis of aryl nitriles, such as benzylic halides, alcohols, amines and azides. Furthermore, the direct conversion of the methyl group of toluene derivatives into a cyano group has also drawn attention. In this critical review, we summarize the recent developments and useful applications in this field and reaction mechanisms are also briefly discussed.

中文翻译：

芳基腈化合物合成的最新进展

在天然产物，药物，农用化学品，染料和除草剂中广泛发现芳基腈。而且，由于氰基可以容易地转化成各种官能团，因此芳基腈是合成有机化学中的重要中间体。因此，对芳基腈的合成新方法的开发引起了极大的兴趣。合成的传统方法包括Sandmeyer反应，Rosnmund–von Braun反应以及醛肟和酰胺的脱水反应。近年来，为芳基（假）卤化物，有机金属试剂和芳基CH键的过渡金属催化的氰化反应做出了许多努力。已经探索了许多用于这种转化的氰化试剂，包括金属氰化物和有机氰基源。此外，苯乙烯和芳基取代的炔烃通过碳-碳双键或三键裂解成功转化为芳基腈。各种苄基化合物也已用于合成芳基腈，例如苄基卤化物，醇，胺和叠氮化物。此外，甲苯衍生物的甲基直接转化为氰基也引起了关注。在这篇重要的综述中，我们总结了该领域的最新发展和有用的应用，并且还简要讨论了反应机理。甲苯衍生物的甲基直接转化成氰基也引起了人们的注意。在这篇重要的综述中，我们总结了该领域的最新发展和有用的应用，并且还简要讨论了反应机理。甲苯衍生物的甲基直接转化成氰基也引起了人们的注意。在这篇重要的综述中，我们总结了该领域的最新发展和有用的应用，并且还简要讨论了反应机理。

更新日期：2017-12-04

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