SET-Induced Biaryl Cross-Coupling: An S(RN)1 Reaction

[Image: see text] The SET-induced biaryl cross-coupling reaction is established as the first example of a Grignard S(RN)1 reaction. The reaction is examined within the mechanistic framework of dissociative electron transfer in the presence of a Lewis acid. DFT calculations show that the reaction pro...

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Detalles Bibliográficos
Autores principales: Haines, Brandon E., Wiest, Olaf
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985438/
https://www.ncbi.nlm.nih.gov/pubmed/24564385
http://dx.doi.org/10.1021/jo500222d
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author Haines, Brandon E.
Wiest, Olaf
author_facet Haines, Brandon E.
Wiest, Olaf
author_sort Haines, Brandon E.
collection PubMed
description [Image: see text] The SET-induced biaryl cross-coupling reaction is established as the first example of a Grignard S(RN)1 reaction. The reaction is examined within the mechanistic framework of dissociative electron transfer in the presence of a Lewis acid. DFT calculations show that the reaction proceeds through a radical intermediate in the form of an Mg ion-radical cage, which eludes detection in trapping experiments by reacting quickly to form an MgPh(2) radical anion intermediate. A new mechanism is proposed.
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spelling pubmed-39854382015-02-24 SET-Induced Biaryl Cross-Coupling: An S(RN)1 Reaction Haines, Brandon E. Wiest, Olaf J Org Chem [Image: see text] The SET-induced biaryl cross-coupling reaction is established as the first example of a Grignard S(RN)1 reaction. The reaction is examined within the mechanistic framework of dissociative electron transfer in the presence of a Lewis acid. DFT calculations show that the reaction proceeds through a radical intermediate in the form of an Mg ion-radical cage, which eludes detection in trapping experiments by reacting quickly to form an MgPh(2) radical anion intermediate. A new mechanism is proposed. American Chemical Society 2014-02-24 2014-03-21 /pmc/articles/PMC3985438/ /pubmed/24564385 http://dx.doi.org/10.1021/jo500222d Text en Copyright © 2014 American Chemical Society
spellingShingle Haines, Brandon E.
Wiest, Olaf
SET-Induced Biaryl Cross-Coupling: An S(RN)1 Reaction
title SET-Induced Biaryl Cross-Coupling: An S(RN)1 Reaction
title_full SET-Induced Biaryl Cross-Coupling: An S(RN)1 Reaction
title_fullStr SET-Induced Biaryl Cross-Coupling: An S(RN)1 Reaction
title_full_unstemmed SET-Induced Biaryl Cross-Coupling: An S(RN)1 Reaction
title_short SET-Induced Biaryl Cross-Coupling: An S(RN)1 Reaction
title_sort set-induced biaryl cross-coupling: an s(rn)1 reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985438/
https://www.ncbi.nlm.nih.gov/pubmed/24564385
http://dx.doi.org/10.1021/jo500222d
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AT wiestolaf setinducedbiarylcrosscouplingansrn1reaction

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