Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides

An expeditious approach to the construction of spiroindenyl-2-oxindoles was developed via a palladium-catalyzed spirocyclization reaction of 2-bromoarylamides with vinyl bromides. The reaction formed spiropalladacycles as the intermediates via carbopalladation and the C–H functionalization of 2-brom...

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Autores principales: Yang, Shuai, Zhang, Yanghui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8704520/
https://www.ncbi.nlm.nih.gov/pubmed/34946579
http://dx.doi.org/10.3390/molecules26247496
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author Yang, Shuai
Zhang, Yanghui
author_facet Yang, Shuai
Zhang, Yanghui
author_sort Yang, Shuai
collection PubMed
description An expeditious approach to the construction of spiroindenyl-2-oxindoles was developed via a palladium-catalyzed spirocyclization reaction of 2-bromoarylamides with vinyl bromides. The reaction formed spiropalladacycles as the intermediates via carbopalladation and the C–H functionalization of 2-bromoarylamides. The spiropalladacycles reacted with vinyl bromides to form spiroindenyl-2-oxindoles. A Heck process rather than vinylic C–H functionalization was involved in the reaction.
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spelling pubmed-87045202021-12-25 Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides Yang, Shuai Zhang, Yanghui Molecules Article An expeditious approach to the construction of spiroindenyl-2-oxindoles was developed via a palladium-catalyzed spirocyclization reaction of 2-bromoarylamides with vinyl bromides. The reaction formed spiropalladacycles as the intermediates via carbopalladation and the C–H functionalization of 2-bromoarylamides. The spiropalladacycles reacted with vinyl bromides to form spiroindenyl-2-oxindoles. A Heck process rather than vinylic C–H functionalization was involved in the reaction. MDPI 2021-12-10 /pmc/articles/PMC8704520/ /pubmed/34946579 http://dx.doi.org/10.3390/molecules26247496 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Yang, Shuai
Zhang, Yanghui
Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides
title Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides
title_full Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides
title_fullStr Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides
title_full_unstemmed Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides
title_short Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides
title_sort synthesis of spiroindenyl-2-oxindoles through palladium-catalyzed spirocyclization of 2-bromoarylamides and vinyl bromides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8704520/
https://www.ncbi.nlm.nih.gov/pubmed/34946579
http://dx.doi.org/10.3390/molecules26247496
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AT zhangyanghui synthesisofspiroindenyl2oxindolesthroughpalladiumcatalyzedspirocyclizationof2bromoarylamidesandvinylbromides

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