Alkene 1,2‐Difunctionalization by Radical Alkenyl Migration

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 regiosel...

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Detalles Bibliográficos
Autores principales: Tang, Xinjun, Studer, Armido
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838557/
https://www.ncbi.nlm.nih.gov/pubmed/29165859
http://dx.doi.org/10.1002/anie.201710397
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author Tang, Xinjun
Studer, Armido
author_facet Tang, Xinjun
Studer, Armido
author_sort Tang, Xinjun
collection PubMed
description 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.
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spelling pubmed-58385572018-03-12 Alkene 1,2‐Difunctionalization by Radical Alkenyl Migration Tang, Xinjun Studer, Armido Angew Chem Int Ed Engl Communications 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. John Wiley and Sons Inc. 2017-12-14 2018-01-15 /pmc/articles/PMC5838557/ /pubmed/29165859 http://dx.doi.org/10.1002/anie.201710397 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Tang, Xinjun
Studer, Armido
Alkene 1,2‐Difunctionalization by Radical Alkenyl Migration
title Alkene 1,2‐Difunctionalization by Radical Alkenyl Migration
title_full Alkene 1,2‐Difunctionalization by Radical Alkenyl Migration
title_fullStr Alkene 1,2‐Difunctionalization by Radical Alkenyl Migration
title_full_unstemmed Alkene 1,2‐Difunctionalization by Radical Alkenyl Migration
title_short Alkene 1,2‐Difunctionalization by Radical Alkenyl Migration
title_sort alkene 1,2‐difunctionalization by radical alkenyl migration
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838557/
https://www.ncbi.nlm.nih.gov/pubmed/29165859
http://dx.doi.org/10.1002/anie.201710397
work_keys_str_mv AT tangxinjun alkene12difunctionalizationbyradicalalkenylmigration
AT studerarmido alkene12difunctionalizationbyradicalalkenylmigration

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