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Alkene 1,2‐Difunctionalization by Radical Alkenyl Migration
Author(s) -
Tang Xinjun,
Studer Armido
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201710397
Subject(s) - chemistry , ketyl , alkene , regioselectivity , allylic rearrangement , deprotonation , reagent , radical ion , vicinal , radical cyclization , nucleophile , photochemistry , catalysis , electron transfer , medicinal chemistry , radical , organic chemistry , ion
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.