Electrosynthesis of β‐Acyloxy‐γ‐Selenyl Amines via Migratory Oxyselenation of <i>N</i>‐Acyl Allylamines
Kejun Lin, Jianyong Lan, Tingshun Zhu
Abstract
Abstract A metal‐free and external‐oxidant‐free electrosynthesis of β‐acyloxy‐γ‐selenyl amines was developed. The cascade reaction is triggered by anodic oxidative generation of electrophilic selenium cation, followed by electrophilic addition to the unactivated alkene, and successive water promoted intramolecular acyl migration. The reactions gave the products in up to 98% yield with controllable regio‐ and diastereoselectivities. Different chemoselectivity towards cyclization products was also viable with N ‐Boc and N‐ Cbz substrates. Both batch chemistry and flow chemistry were available for scale‐up synthesis with up to 91% yield. magnified image
Topics & Concepts
ChemistryElectrosynthesisChemoselectivityElectrophileAlkeneAcylationYield (engineering)Intramolecular forceOrganic chemistryFlow chemistryCombinatorial chemistryCatalysisElectrochemistryPhysical chemistryElectrodeMetallurgyMaterials scienceSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsOrganoselenium and organotellurium chemistry