Yurino Taiga, Ohkuma Takeshi
Division of Applied Chemistry and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Kita 13, Nishi 8, Sapporo, Hokkaido 060-8628, Japan.
ACS Omega. 2020 Mar 9;5(10):4719-4724. doi: 10.1021/acsomega.9b04073. eCollection 2020 Mar 17.
Isonitriles are frequently employed as both substrates for organic transformations and ligands for organometallic chemistry. However, despite the wide application of the isonitriles, their synthesis generally depends on the traditional dehydration of -formamide. "Nucleophilic isocyanation" using cyanide as an -nucleophile is another straightforward strategy affording the corresponding isonitriles. This method has been available since the 19th century but is still an immature procedure and is therefore more rarely used. In this review, we summarize the concepts and recent progress in nucleophilic isocyanation, including the relatively rare examples of catalytic isocyanation.
异腈类化合物经常被用作有机转化的底物以及有机金属化学中的配体。然而,尽管异腈类化合物有着广泛的应用,它们的合成通常依赖于传统的甲酰胺脱水反应。使用氰化物作为亲核试剂的“亲核异氰化反应”是另一种直接合成相应异腈类化合物的策略。该方法自19世纪就已出现,但仍是一个不成熟的过程,因此较少被使用。在这篇综述中,我们总结了亲核异氰化反应的概念和最新进展,包括相对罕见的催化异氰化反应实例。