Atom-efficient transition-metal-free arylation of N,O-acetals using diarylzinc reagents through Zn/Zn cooperativity

Exploiting the cooperative action of Lewis acid Zn(C(6)F(5))(2) with diarylzinc reagents, the efficient arylation of N,O-acetals to access diarylmethylamines is reported. Reactions take place under mild reaction conditions without the need for transtion-metal catalysis. Mechanistic investigations ha...

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Autores principales: Borys, Andryj M., Gil-Negrete, Jose M., Hevia, Eva
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8419782/
https://www.ncbi.nlm.nih.gov/pubmed/34486629
http://dx.doi.org/10.1039/d1cc04137a
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author Borys, Andryj M.
Gil-Negrete, Jose M.
Hevia, Eva
author_facet Borys, Andryj M.
Gil-Negrete, Jose M.
Hevia, Eva
author_sort Borys, Andryj M.
collection PubMed
description Exploiting the cooperative action of Lewis acid Zn(C(6)F(5))(2) with diarylzinc reagents, the efficient arylation of N,O-acetals to access diarylmethylamines is reported. Reactions take place under mild reaction conditions without the need for transtion-metal catalysis. Mechanistic investigations have revealed that Zn(C(6)F(5))(2) not only acts as a Lewis acid activator, but also enables the regeneration of nucleophilic ZnAr(2) species, allowing a limiting 50 mol% to be employed.
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spelling pubmed-84197822021-09-28 Atom-efficient transition-metal-free arylation of N,O-acetals using diarylzinc reagents through Zn/Zn cooperativity Borys, Andryj M. Gil-Negrete, Jose M. Hevia, Eva Chem Commun (Camb) Chemistry Exploiting the cooperative action of Lewis acid Zn(C(6)F(5))(2) with diarylzinc reagents, the efficient arylation of N,O-acetals to access diarylmethylamines is reported. Reactions take place under mild reaction conditions without the need for transtion-metal catalysis. Mechanistic investigations have revealed that Zn(C(6)F(5))(2) not only acts as a Lewis acid activator, but also enables the regeneration of nucleophilic ZnAr(2) species, allowing a limiting 50 mol% to be employed. The Royal Society of Chemistry 2021-08-11 /pmc/articles/PMC8419782/ /pubmed/34486629 http://dx.doi.org/10.1039/d1cc04137a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Borys, Andryj M.
Gil-Negrete, Jose M.
Hevia, Eva
Atom-efficient transition-metal-free arylation of N,O-acetals using diarylzinc reagents through Zn/Zn cooperativity
title Atom-efficient transition-metal-free arylation of N,O-acetals using diarylzinc reagents through Zn/Zn cooperativity
title_full Atom-efficient transition-metal-free arylation of N,O-acetals using diarylzinc reagents through Zn/Zn cooperativity
title_fullStr Atom-efficient transition-metal-free arylation of N,O-acetals using diarylzinc reagents through Zn/Zn cooperativity
title_full_unstemmed Atom-efficient transition-metal-free arylation of N,O-acetals using diarylzinc reagents through Zn/Zn cooperativity
title_short Atom-efficient transition-metal-free arylation of N,O-acetals using diarylzinc reagents through Zn/Zn cooperativity
title_sort atom-efficient transition-metal-free arylation of n,o-acetals using diarylzinc reagents through zn/zn cooperativity
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8419782/
https://www.ncbi.nlm.nih.gov/pubmed/34486629
http://dx.doi.org/10.1039/d1cc04137a
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