Atom-efficient arylation of N-tosylimines mediated by cooperative ZnAr(2)/Zn(C(6)F(5))(2) combinations

By combining the Lewis acid Zn(C(6)F(5))(2) with nucleophilic diarylzinc (ZnAr(2)) reagents, we report the atom-efficient arylation of N-tosylimines under mild conditions. Mechanistic studies through the isolation of key intermediates reveal how the two zinc species act cooperatively to activate the...

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Autores principales: Borys, Andryj M., Kunzmann, Tim, Gil-Negrete, Jose M., Hevia, Eva
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10270240/
https://www.ncbi.nlm.nih.gov/pubmed/37254841
http://dx.doi.org/10.1039/d3cc01490h
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author Borys, Andryj M.
Kunzmann, Tim
Gil-Negrete, Jose M.
Hevia, Eva
author_facet Borys, Andryj M.
Kunzmann, Tim
Gil-Negrete, Jose M.
Hevia, Eva
author_sort Borys, Andryj M.
collection PubMed
description By combining the Lewis acid Zn(C(6)F(5))(2) with nucleophilic diarylzinc (ZnAr(2)) reagents, we report the atom-efficient arylation of N-tosylimines under mild conditions. Mechanistic studies through the isolation of key intermediates reveal how the two zinc species act cooperatively to activate the imine substrate and regenerate the ZnAr(2) reagent, enabling a limiting 50 mol% to be employed.
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spelling pubmed-102702402023-06-16 Atom-efficient arylation of N-tosylimines mediated by cooperative ZnAr(2)/Zn(C(6)F(5))(2) combinations Borys, Andryj M. Kunzmann, Tim Gil-Negrete, Jose M. Hevia, Eva Chem Commun (Camb) Chemistry By combining the Lewis acid Zn(C(6)F(5))(2) with nucleophilic diarylzinc (ZnAr(2)) reagents, we report the atom-efficient arylation of N-tosylimines under mild conditions. Mechanistic studies through the isolation of key intermediates reveal how the two zinc species act cooperatively to activate the imine substrate and regenerate the ZnAr(2) reagent, enabling a limiting 50 mol% to be employed. The Royal Society of Chemistry 2023-05-15 /pmc/articles/PMC10270240/ /pubmed/37254841 http://dx.doi.org/10.1039/d3cc01490h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Borys, Andryj M.
Kunzmann, Tim
Gil-Negrete, Jose M.
Hevia, Eva
Atom-efficient arylation of N-tosylimines mediated by cooperative ZnAr(2)/Zn(C(6)F(5))(2) combinations
title Atom-efficient arylation of N-tosylimines mediated by cooperative ZnAr(2)/Zn(C(6)F(5))(2) combinations
title_full Atom-efficient arylation of N-tosylimines mediated by cooperative ZnAr(2)/Zn(C(6)F(5))(2) combinations
title_fullStr Atom-efficient arylation of N-tosylimines mediated by cooperative ZnAr(2)/Zn(C(6)F(5))(2) combinations
title_full_unstemmed Atom-efficient arylation of N-tosylimines mediated by cooperative ZnAr(2)/Zn(C(6)F(5))(2) combinations
title_short Atom-efficient arylation of N-tosylimines mediated by cooperative ZnAr(2)/Zn(C(6)F(5))(2) combinations
title_sort atom-efficient arylation of n-tosylimines mediated by cooperative znar(2)/zn(c(6)f(5))(2) combinations
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10270240/
https://www.ncbi.nlm.nih.gov/pubmed/37254841
http://dx.doi.org/10.1039/d3cc01490h
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