Arynes as Radical Acceptors: TEMPO‐Mediated Cascades Comprising Addition, Cyclization, and Trapping

The application of arynes as radical acceptors is described. The stable radical TEMPO (2,2,6,6‐tetramethyl piperidine 1‐oxyl) is shown to add to various ortho‐substituted benzynes generating the corresponding aryl radicals which engage in 5‐exo or 6‐endo cyclizations. The cyclized radicals are event...

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Autores principales: Scherübl, Maximilian, Daniliuc, Constantin G., Studer, Armido
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7839731/
https://www.ncbi.nlm.nih.gov/pubmed/33038065
http://dx.doi.org/10.1002/anie.202012654
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author Scherübl, Maximilian
Daniliuc, Constantin G.
Studer, Armido
author_facet Scherübl, Maximilian
Daniliuc, Constantin G.
Studer, Armido
author_sort Scherübl, Maximilian
collection PubMed
description The application of arynes as radical acceptors is described. The stable radical TEMPO (2,2,6,6‐tetramethyl piperidine 1‐oxyl) is shown to add to various ortho‐substituted benzynes generating the corresponding aryl radicals which engage in 5‐exo or 6‐endo cyclizations. The cyclized radicals are eventually trapped by TEMPO. The introduced method provides ready access to various dihydrobenzofurans, oxindoles, and sultones by a conceptually novel approach.
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spelling pubmed-78397312021-02-02 Arynes as Radical Acceptors: TEMPO‐Mediated Cascades Comprising Addition, Cyclization, and Trapping Scherübl, Maximilian Daniliuc, Constantin G. Studer, Armido Angew Chem Int Ed Engl Communications The application of arynes as radical acceptors is described. The stable radical TEMPO (2,2,6,6‐tetramethyl piperidine 1‐oxyl) is shown to add to various ortho‐substituted benzynes generating the corresponding aryl radicals which engage in 5‐exo or 6‐endo cyclizations. The cyclized radicals are eventually trapped by TEMPO. The introduced method provides ready access to various dihydrobenzofurans, oxindoles, and sultones by a conceptually novel approach. John Wiley and Sons Inc. 2020-12-10 2021-01-11 /pmc/articles/PMC7839731/ /pubmed/33038065 http://dx.doi.org/10.1002/anie.202012654 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the 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
Scherübl, Maximilian
Daniliuc, Constantin G.
Studer, Armido
Arynes as Radical Acceptors: TEMPO‐Mediated Cascades Comprising Addition, Cyclization, and Trapping
title Arynes as Radical Acceptors: TEMPO‐Mediated Cascades Comprising Addition, Cyclization, and Trapping
title_full Arynes as Radical Acceptors: TEMPO‐Mediated Cascades Comprising Addition, Cyclization, and Trapping
title_fullStr Arynes as Radical Acceptors: TEMPO‐Mediated Cascades Comprising Addition, Cyclization, and Trapping
title_full_unstemmed Arynes as Radical Acceptors: TEMPO‐Mediated Cascades Comprising Addition, Cyclization, and Trapping
title_short Arynes as Radical Acceptors: TEMPO‐Mediated Cascades Comprising Addition, Cyclization, and Trapping
title_sort arynes as radical acceptors: tempo‐mediated cascades comprising addition, cyclization, and trapping
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7839731/
https://www.ncbi.nlm.nih.gov/pubmed/33038065
http://dx.doi.org/10.1002/anie.202012654
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