Regio‐ and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles

Herein, we report a regioselective alkenyl electrophile synthesis from unactivated olefins that is based on a direct and regioselective C−H thianthrenation reaction. The selectivity is proposed to arise from an unusual inverse‐electron‐demand hetero‐Diels–Alder reaction. The alkenyl sulfonium salts...

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Detalles Bibliográficos
Autores principales: Chen, Junting, Li, Jiakun, Plutschack, Matthew B., Berger, Florian, Ritter, Tobias
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/PMC7154751/
https://www.ncbi.nlm.nih.gov/pubmed/31782968
http://dx.doi.org/10.1002/anie.201914215
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author Chen, Junting
Li, Jiakun
Plutschack, Matthew B.
Berger, Florian
Ritter, Tobias
author_facet Chen, Junting
Li, Jiakun
Plutschack, Matthew B.
Berger, Florian
Ritter, Tobias
author_sort Chen, Junting
collection PubMed
description Herein, we report a regioselective alkenyl electrophile synthesis from unactivated olefins that is based on a direct and regioselective C−H thianthrenation reaction. The selectivity is proposed to arise from an unusual inverse‐electron‐demand hetero‐Diels–Alder reaction. The alkenyl sulfonium salts can serve as electrophiles in palladium‐ and ruthenium‐catalyzed cross‐coupling reactions to make alkenyl C−C, C−Cl, C−Br, and C−SCF(3) bonds with stereoretention.
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spelling pubmed-71547512020-04-15 Regio‐ and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles Chen, Junting Li, Jiakun Plutschack, Matthew B. Berger, Florian Ritter, Tobias Angew Chem Int Ed Engl Communications Herein, we report a regioselective alkenyl electrophile synthesis from unactivated olefins that is based on a direct and regioselective C−H thianthrenation reaction. The selectivity is proposed to arise from an unusual inverse‐electron‐demand hetero‐Diels–Alder reaction. The alkenyl sulfonium salts can serve as electrophiles in palladium‐ and ruthenium‐catalyzed cross‐coupling reactions to make alkenyl C−C, C−Cl, C−Br, and C−SCF(3) bonds with stereoretention. John Wiley and Sons Inc. 2020-02-03 2020-03-27 /pmc/articles/PMC7154751/ /pubmed/31782968 http://dx.doi.org/10.1002/anie.201914215 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Chen, Junting
Li, Jiakun
Plutschack, Matthew B.
Berger, Florian
Ritter, Tobias
Regio‐ and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles
title Regio‐ and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles
title_full Regio‐ and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles
title_fullStr Regio‐ and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles
title_full_unstemmed Regio‐ and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles
title_short Regio‐ and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles
title_sort regio‐ and stereoselective thianthrenation of olefins to access versatile alkenyl electrophiles
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7154751/
https://www.ncbi.nlm.nih.gov/pubmed/31782968
http://dx.doi.org/10.1002/anie.201914215
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