Key Laboratory of Biopesticide and Chemical Biology (Ministry of Education), College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou 350002, Fujian, China.
Guangdong Key Laboratory of Animal Conservation and Resource Utilization, Guangdong Public Laboratory of Wild Animal Conservation and Utilization, Institute of Zoology, Guangdong Academy of Sciences, Guangzhou 510275, Guangdong, China.
J Org Chem. 2022 Aug 5;87(15):10550-10554. doi: 10.1021/acs.joc.2c01391. Epub 2022 Jul 22.
Nitrile imines are highly reactive and versatile dipoles and conventionally generated from unstable hydrazonyl halides under basic conditions. Herein, we report the first green and user-friendly protocol for generation of nitrile imines from Oxone-KBr oxidation of hydrazones and base-promoted dehydrobromination. The nitrile imines were demonstrated for 1,3-dipolar cycloaddition with various dipolarophiles, including alkene and alkyne groups. With its green nature, ease of operation, and air and moisture tolerance, we expect our method will find wide applications in organic synthesis.
腈亚胺是高反应性和多功能的偶极子，通常在碱性条件下由不稳定的重氮盐卤化物生成。在此，我们报告了第一个从水合腙的 Oxone-KBr 氧化和碱促进的脱溴化作用生成腈亚胺的绿色、友好型方法。腈亚胺被证明可与各种偶极子进行 1,3-偶极环加成反应，包括烯烃和炔烃基团。由于其绿色特性、操作简便、对空气和水分的耐受性，我们预计该方法将在有机合成中得到广泛应用。
