Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes
作者:Zhichao Lu、Olivia Hennis、Joseph Gentry、Bo Xu、Gerald B. Hammond
DOI:10.1021/acs.orglett.0c01395
日期:2020.6.5
The base-inducedreaction of aryl diazonium salts with commercially available CF3SO2Na/CF2HSO2Na allows for the generation of the corresponding diazene radicals along with fluoromethyl radicals. The addition of fluoromethyl radicals to alkenes with subsequent diazene trapping provides the azofluoromethylation products in good to excellent yields. This metal-free method under mild reaction conditions
芳基重氮盐与可商购获得的CF 3 SO 2 Na / CF 2 HSO 2 Na的碱诱导反应可以生成相应的重氮基和氟甲基。将氟甲基自由基加到烯烃中,随后进行重氮捕集,可提供良好至极佳收率的偶氮氟甲基化产物。这种在温和反应条件下的无金属方法具有广泛的官能团相容性,可用于各种天然产物和生物活性分子的后期修饰。
(Radio)Fluoro-iodination of Alkenes Enabled by a Hydrogen Bonding Donor Solvent
We have developed a widely applicable (radio)fluoro-iodination of alkenes using readily available and easily handled KF (18F). The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Furthermore, the resulting product could be further functionalized with various nucleophiles.