Sulfoxide-mediated oxidative cross-coupling of phenols

A metal-free, oxidative coupling of phenols with various nucleophiles, including arenes, 1,3-diketones and other phenols, is reported. Cross-coupling is mediated by a sulfoxide which inverts the reactivity of the phenol partner. Crucially, the process shows high selectivity for cross-versus homo-cou...

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Detalles Bibliográficos
Autores principales: He, Zhen, Perry, Gregory J. P., Procter, David J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8150100/
https://www.ncbi.nlm.nih.gov/pubmed/34123295
http://dx.doi.org/10.1039/c9sc05668h
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author He, Zhen
Perry, Gregory J. P.
Procter, David J.
author_facet He, Zhen
Perry, Gregory J. P.
Procter, David J.
author_sort He, Zhen
collection PubMed
description A metal-free, oxidative coupling of phenols with various nucleophiles, including arenes, 1,3-diketones and other phenols, is reported. Cross-coupling is mediated by a sulfoxide which inverts the reactivity of the phenol partner. Crucially, the process shows high selectivity for cross-versus homo-coupling and allows efficient access to a variety of aromatic scaffolds including biaryls, benzofurans and, through an iterative procedure, aromatic oligomers.
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spelling pubmed-81501002021-06-11 Sulfoxide-mediated oxidative cross-coupling of phenols He, Zhen Perry, Gregory J. P. Procter, David J. Chem Sci Chemistry A metal-free, oxidative coupling of phenols with various nucleophiles, including arenes, 1,3-diketones and other phenols, is reported. Cross-coupling is mediated by a sulfoxide which inverts the reactivity of the phenol partner. Crucially, the process shows high selectivity for cross-versus homo-coupling and allows efficient access to a variety of aromatic scaffolds including biaryls, benzofurans and, through an iterative procedure, aromatic oligomers. The Royal Society of Chemistry 2020-01-15 /pmc/articles/PMC8150100/ /pubmed/34123295 http://dx.doi.org/10.1039/c9sc05668h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
He, Zhen
Perry, Gregory J. P.
Procter, David J.
Sulfoxide-mediated oxidative cross-coupling of phenols
title Sulfoxide-mediated oxidative cross-coupling of phenols
title_full Sulfoxide-mediated oxidative cross-coupling of phenols
title_fullStr Sulfoxide-mediated oxidative cross-coupling of phenols
title_full_unstemmed Sulfoxide-mediated oxidative cross-coupling of phenols
title_short Sulfoxide-mediated oxidative cross-coupling of phenols
title_sort sulfoxide-mediated oxidative cross-coupling of phenols
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8150100/
https://www.ncbi.nlm.nih.gov/pubmed/34123295
http://dx.doi.org/10.1039/c9sc05668h
work_keys_str_mv AT hezhen sulfoxidemediatedoxidativecrosscouplingofphenols
AT perrygregoryjp sulfoxidemediatedoxidativecrosscouplingofphenols
AT procterdavidj sulfoxidemediatedoxidativecrosscouplingofphenols

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