National Research Center for Carbohydrate Synthesis and Jiangxi Province Key Laboratory of Chemical Biology, Jiangxi Normal University, Nanchang, 330022, Jiangxi, P. R. China.
College of Traditional Chinese Medicine, Jiangxi University of Chinese Medicine, Nanchang, 330022, Jiangxi, P. R. China.
Nat Commun. 2022 Jul 30;13(1):4430. doi: 10.1038/s41467-022-32084-8.
1,2-Amino oxygenation of alkenes has emerged as one of the most straightforward synthetic methods to produce β-amino alcohols, which are important organic building blocks. Thus, a practical synthetic strategy for 1,2-amino oxygenation is highly desirable. Here, we reported an electro-oxidative intermolecular 1,2-amino oxygenation of alkenes with hydrogen evolution, removing the requirement of extra-oxidant. Using commercial oxygen and nitrogen sources as starting materials, this method provides a cheap, scalable, and efficient route to a set of valuable β-amino alcohol derivatives. Moreover, the merit of this protocol has been exhibited by its broad substrate scope and good application in continuous-flow reactors. Furthermore, this method can be extended to other amino-functionalization of alkenes, thereby showing the potential to inspire advances in applications of electro-induced N-centered radicals (NCRs).
1,2-氨基氧化烯烃已成为合成β-氨基醇的最直接的方法之一，而β-氨基醇是重要的有机砌块。因此，开发实用的 1,2-氨基氧化方法具有很高的需求。在这里，我们报道了一种电氧化的烯烃分子间 1,2-氨基氧化反应，同时伴随着氢气的析出，从而消除了对额外氧化剂的需求。该方法以商业氧气和氮气源为起始原料，为一系列有价值的β-氨基醇衍生物提供了一种廉价、可扩展且高效的合成路线。此外，该方法还具有广泛的底物范围和在连续流反应器中的良好应用，证明了其优势。进一步地，该方法可以扩展到其他烯烃的氨基官能化，从而显示出在电诱导 N 中心自由基（NCRs）应用方面的潜力。
