Manchester Metropolitan University, Faculty of Science and Engineering, School of Science and the Environment, Division of Chemistry and Environmental Science, John Dalton Building, Chester Street, Manchester, M1 5GD, UK.
Beilstein J Org Chem. 2014 Dec 18;10:3056-72. doi: 10.3762/bjoc.10.323. eCollection 2014.
N-acyliminium ions are useful reactive synthetic intermediates in a variety of important carbon-carbon bond forming and cyclisation strategies in organic chemistry. The advent of an electrochemical anodic oxidation of unfunctionalised amides, more commonly known as the Shono oxidation, has provided a complementary route to the C-H activation of low reactivity intermediates. In this article, containing over 100 references, we highlight the development of the Shono-type oxidations from the original direct electrolysis methods, to the use of electroauxiliaries before arriving at indirect electrolysis methodologies. We also highlight new technologies and techniques applied to this area of electrosynthesis. We conclude with the use of this electrosynthetic approach to challenging syntheses of natural products and other complex structures for biological evaluation discussing recent technological developments in electroorganic techniques and future directions.
N-酰亚胺离子是有机化学中多种重要的碳-碳键形成和环化策略中有用的反应性合成中间体。电化学阳极氧化未官能化酰胺的出现，通常称为 Shono 氧化，为低反应性中间体的 C-H 活化提供了一种补充途径。在本文中，我们引用了 100 多篇参考文献，重点介绍了 Shono 型氧化反应从最初的直接电解方法，到使用电辅助试剂，再到间接电解方法的发展。我们还强调了应用于该电合成领域的新技术和技术。最后，我们讨论了电有机技术的最新技术发展和未来方向，以及使用这种电合成方法对具有挑战性的天然产物和其他复杂结构的合成进行生物评价。
