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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201710397
Subject(s) - ketyl , alkene , chemistry , regioselectivity , deprotonation , allylic rearrangement , reagent , radical ion , vicinal , catalysis , radical cyclization , nucleophile , electron transfer , photochemistry , radical , medicinal chemistry , combinatorial chemistry , 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.