Pd-Catalyzed 1,3-Alkenylarylation of Skipped Diene via Metal Migration

[Image: see text] We disclose a palladium-catalyzed difunctionalization of skipped diene with alkenyl triflates and arylboronic acids to produce 1,3-alkenylarylated products. The reaction proceeded efficiently with Pd(acac)(2) as a catalyst and CsF as a base for a wide range of electron-deficient an...

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Autores principales: Chesley, Lucas J., Poudel, Dhruba P., Sapkota, Rishi R., Dhungana, Roshan K., Lakomy, Margaret G., Giri, Ramesh
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10249098/
https://www.ncbi.nlm.nih.gov/pubmed/37305246
http://dx.doi.org/10.1021/acsomega.3c01839
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author Chesley, Lucas J.
Poudel, Dhruba P.
Sapkota, Rishi R.
Dhungana, Roshan K.
Lakomy, Margaret G.
Giri, Ramesh
author_facet Chesley, Lucas J.
Poudel, Dhruba P.
Sapkota, Rishi R.
Dhungana, Roshan K.
Lakomy, Margaret G.
Giri, Ramesh
author_sort Chesley, Lucas J.
collection PubMed
description [Image: see text] We disclose a palladium-catalyzed difunctionalization of skipped diene with alkenyl triflates and arylboronic acids to produce 1,3-alkenylarylated products. The reaction proceeded efficiently with Pd(acac)(2) as a catalyst and CsF as a base for a wide range of electron-deficient and electron-rich arylboronic acids as well as oxygen-heterocyclic, sterically hindered, and complex natural product-derived alkenyl triflates bearing various functional groups. The reaction produced 3-aryl-5-alkenylcyclohexene derivatives with 1,3-syn-disubstituted stereochemistry.
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spelling pubmed-102490982023-06-09 Pd-Catalyzed 1,3-Alkenylarylation of Skipped Diene via Metal Migration Chesley, Lucas J. Poudel, Dhruba P. Sapkota, Rishi R. Dhungana, Roshan K. Lakomy, Margaret G. Giri, Ramesh ACS Omega [Image: see text] We disclose a palladium-catalyzed difunctionalization of skipped diene with alkenyl triflates and arylboronic acids to produce 1,3-alkenylarylated products. The reaction proceeded efficiently with Pd(acac)(2) as a catalyst and CsF as a base for a wide range of electron-deficient and electron-rich arylboronic acids as well as oxygen-heterocyclic, sterically hindered, and complex natural product-derived alkenyl triflates bearing various functional groups. The reaction produced 3-aryl-5-alkenylcyclohexene derivatives with 1,3-syn-disubstituted stereochemistry. American Chemical Society 2023-05-25 /pmc/articles/PMC10249098/ /pubmed/37305246 http://dx.doi.org/10.1021/acsomega.3c01839 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Chesley, Lucas J.
Poudel, Dhruba P.
Sapkota, Rishi R.
Dhungana, Roshan K.
Lakomy, Margaret G.
Giri, Ramesh
Pd-Catalyzed 1,3-Alkenylarylation of Skipped Diene via Metal Migration
title Pd-Catalyzed 1,3-Alkenylarylation of Skipped Diene via Metal Migration
title_full Pd-Catalyzed 1,3-Alkenylarylation of Skipped Diene via Metal Migration
title_fullStr Pd-Catalyzed 1,3-Alkenylarylation of Skipped Diene via Metal Migration
title_full_unstemmed Pd-Catalyzed 1,3-Alkenylarylation of Skipped Diene via Metal Migration
title_short Pd-Catalyzed 1,3-Alkenylarylation of Skipped Diene via Metal Migration
title_sort pd-catalyzed 1,3-alkenylarylation of skipped diene via metal migration
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10249098/
https://www.ncbi.nlm.nih.gov/pubmed/37305246
http://dx.doi.org/10.1021/acsomega.3c01839
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