Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts

[Image: see text] Herein we present a Bi-catalyzed cross-coupling of arylboronic acids with perfluoroalkyl sulfonate salts based on a Bi(III)/Bi(V) redox cycle. An electron-deficient sulfone ligand proved to be key for the successful implementation of this protocol, which allows the unusual construc...

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Autores principales: Planas, Oriol, Peciukenas, Vytautas, Cornella, Josep
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7315642/
https://www.ncbi.nlm.nih.gov/pubmed/32536157
http://dx.doi.org/10.1021/jacs.0c05343
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author Planas, Oriol
Peciukenas, Vytautas
Cornella, Josep
author_facet Planas, Oriol
Peciukenas, Vytautas
Cornella, Josep
author_sort Planas, Oriol
collection PubMed
description [Image: see text] Herein we present a Bi-catalyzed cross-coupling of arylboronic acids with perfluoroalkyl sulfonate salts based on a Bi(III)/Bi(V) redox cycle. An electron-deficient sulfone ligand proved to be key for the successful implementation of this protocol, which allows the unusual construction of C(sp(2))–O bonds using commercially available NaOTf and KONf as coupling partners. Preliminary mechanistic studies as well as theoretical investigations reveal the intermediacy of a highly electrophilic Bi(V) species, which rapidly eliminates phenyl triflate.
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spelling pubmed-73156422020-06-26 Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts Planas, Oriol Peciukenas, Vytautas Cornella, Josep J Am Chem Soc [Image: see text] Herein we present a Bi-catalyzed cross-coupling of arylboronic acids with perfluoroalkyl sulfonate salts based on a Bi(III)/Bi(V) redox cycle. An electron-deficient sulfone ligand proved to be key for the successful implementation of this protocol, which allows the unusual construction of C(sp(2))–O bonds using commercially available NaOTf and KONf as coupling partners. Preliminary mechanistic studies as well as theoretical investigations reveal the intermediacy of a highly electrophilic Bi(V) species, which rapidly eliminates phenyl triflate. American Chemical Society 2020-06-14 2020-07-01 /pmc/articles/PMC7315642/ /pubmed/32536157 http://dx.doi.org/10.1021/jacs.0c05343 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Planas, Oriol
Peciukenas, Vytautas
Cornella, Josep
Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts
title Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts
title_full Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts
title_fullStr Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts
title_full_unstemmed Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts
title_short Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts
title_sort bismuth-catalyzed oxidative coupling of arylboronic acids with triflate and nonaflate salts
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7315642/
https://www.ncbi.nlm.nih.gov/pubmed/32536157
http://dx.doi.org/10.1021/jacs.0c05343
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