trans-Dichlorobis(XPhos)palladium(II) Precatalyst for Suzuki–Miyaura Cross-Coupling Reactions of Aryl/Vinyl Sulfonates/Halides: Scope, Mechanistic Study, and Synthetic Applications

[Image: see text] Suzuki–Miyaura cross-coupling reactions of aryl/vinyl sulfonates/halides with various boron species were performed using an easily available trans-dichlorobis(XPhos)palladium(II) precatalyst. Under microwave assistance, more than 30 coupling products were obtained with yields rangi...

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Autores principales: Sirindil, Fatih, Pertschi, Romain, Naulin, Emma, Hatey, Delphine, Weibel, Jean-Marc, Pale, Patrick, Blanc, Aurélien
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8756804/
https://www.ncbi.nlm.nih.gov/pubmed/35036781
http://dx.doi.org/10.1021/acsomega.1c05770
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author Sirindil, Fatih
Pertschi, Romain
Naulin, Emma
Hatey, Delphine
Weibel, Jean-Marc
Pale, Patrick
Blanc, Aurélien
author_facet Sirindil, Fatih
Pertschi, Romain
Naulin, Emma
Hatey, Delphine
Weibel, Jean-Marc
Pale, Patrick
Blanc, Aurélien
author_sort Sirindil, Fatih
collection PubMed
description [Image: see text] Suzuki–Miyaura cross-coupling reactions of aryl/vinyl sulfonates/halides with various boron species were performed using an easily available trans-dichlorobis(XPhos)palladium(II) precatalyst. Under microwave assistance, more than 30 coupling products were obtained with yields ranging from 23 to 99%, including the synthesis of two bioactive compounds, dubamine and tamoxifen. A mechanistic investigation of the Suzuki–Miyaura reaction was conducted notably by nuclear magnetic resonance (NMR) and high-resolution mass spectroscopy, revealing the nature of the active Pd(0) species and of the reducing entity.
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spelling pubmed-87568042022-01-13 trans-Dichlorobis(XPhos)palladium(II) Precatalyst for Suzuki–Miyaura Cross-Coupling Reactions of Aryl/Vinyl Sulfonates/Halides: Scope, Mechanistic Study, and Synthetic Applications Sirindil, Fatih Pertschi, Romain Naulin, Emma Hatey, Delphine Weibel, Jean-Marc Pale, Patrick Blanc, Aurélien ACS Omega [Image: see text] Suzuki–Miyaura cross-coupling reactions of aryl/vinyl sulfonates/halides with various boron species were performed using an easily available trans-dichlorobis(XPhos)palladium(II) precatalyst. Under microwave assistance, more than 30 coupling products were obtained with yields ranging from 23 to 99%, including the synthesis of two bioactive compounds, dubamine and tamoxifen. A mechanistic investigation of the Suzuki–Miyaura reaction was conducted notably by nuclear magnetic resonance (NMR) and high-resolution mass spectroscopy, revealing the nature of the active Pd(0) species and of the reducing entity. American Chemical Society 2021-12-23 /pmc/articles/PMC8756804/ /pubmed/35036781 http://dx.doi.org/10.1021/acsomega.1c05770 Text en © 2021 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 Sirindil, Fatih
Pertschi, Romain
Naulin, Emma
Hatey, Delphine
Weibel, Jean-Marc
Pale, Patrick
Blanc, Aurélien
trans-Dichlorobis(XPhos)palladium(II) Precatalyst for Suzuki–Miyaura Cross-Coupling Reactions of Aryl/Vinyl Sulfonates/Halides: Scope, Mechanistic Study, and Synthetic Applications
title trans-Dichlorobis(XPhos)palladium(II) Precatalyst for Suzuki–Miyaura Cross-Coupling Reactions of Aryl/Vinyl Sulfonates/Halides: Scope, Mechanistic Study, and Synthetic Applications
title_full trans-Dichlorobis(XPhos)palladium(II) Precatalyst for Suzuki–Miyaura Cross-Coupling Reactions of Aryl/Vinyl Sulfonates/Halides: Scope, Mechanistic Study, and Synthetic Applications
title_fullStr trans-Dichlorobis(XPhos)palladium(II) Precatalyst for Suzuki–Miyaura Cross-Coupling Reactions of Aryl/Vinyl Sulfonates/Halides: Scope, Mechanistic Study, and Synthetic Applications
title_full_unstemmed trans-Dichlorobis(XPhos)palladium(II) Precatalyst for Suzuki–Miyaura Cross-Coupling Reactions of Aryl/Vinyl Sulfonates/Halides: Scope, Mechanistic Study, and Synthetic Applications
title_short trans-Dichlorobis(XPhos)palladium(II) Precatalyst for Suzuki–Miyaura Cross-Coupling Reactions of Aryl/Vinyl Sulfonates/Halides: Scope, Mechanistic Study, and Synthetic Applications
title_sort trans-dichlorobis(xphos)palladium(ii) precatalyst for suzuki–miyaura cross-coupling reactions of aryl/vinyl sulfonates/halides: scope, mechanistic study, and synthetic applications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8756804/
https://www.ncbi.nlm.nih.gov/pubmed/35036781
http://dx.doi.org/10.1021/acsomega.1c05770
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