Alkene 1, 2‐Difunctionalization by Radical Alkenyl Migration. Issue 3 (14th December 2017)

• Record Type: Journal Article
• Authors: Tang, Xinjun; Studer, Armido
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 3(2018)
• Page Start: 814
• Page End: 817
• Publication Date: 2017-12-14
• Subjects: alkenes -- alkenyl migration -- alkenylation -- perfluoroalkylation -- single-electron transfer; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201710397
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Transition‐metal‐free radical α‐perfluoroalkylation with the accompanying vicinal β‐alkenylation of unactivated alkenes is presented. These radical cascades proceed by means of 1, 4‐ or 1, 5‐alkenyl migration by electron catalysis on readily accessed allylic alcohols. The reactions comprise a regioselective perfluoroalkyl radical addition with subsequent alkenyl migration and concomitant deprotonation to generate a ketyl radical anion that sustains the chain as a single‐electron‐transfer reducing reagent. Abstract : Electron‐catalyzed transition‐metal‐free β‐alkenylation‐α‐perfluoroalkylation of unactivated alkenes by radical 1, 4‐ or 1, 5‐alkenyl migration is presented. Remote radical alkenyl migration is currently not established in synthetic methodology and this Communication documents its potential. DABCO=1, 4‐diazabicyclo[2.2.2]octane; DCE=dichloroethane.