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Catalytic Preparation of 1-Aryl-Substituted 1,2,4-Triazolium Salts

[Image: see text] 1,4-Diaryl- and 1-aryl-4-alkyl-substituted 1,2,4-triazolium salts are convenient air-stable precursors to carbenes used both as organocatalysts or as ligands for transition metal complexes. Traditionally, they are prepared via a multistep synthetic pathway with the low-yielding for...

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Autores principales: Hutchinson, Scott M., Ardón-Muñoz, Luis G., Ratliff, Margarita L., Bolliger, Jeanne L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6822220/
https://www.ncbi.nlm.nih.gov/pubmed/31681902
http://dx.doi.org/10.1021/acsomega.9b03109
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author Hutchinson, Scott M.
Ardón-Muñoz, Luis G.
Ratliff, Margarita L.
Bolliger, Jeanne L.
author_facet Hutchinson, Scott M.
Ardón-Muñoz, Luis G.
Ratliff, Margarita L.
Bolliger, Jeanne L.
author_sort Hutchinson, Scott M.
collection PubMed
description [Image: see text] 1,4-Diaryl- and 1-aryl-4-alkyl-substituted 1,2,4-triazolium salts are convenient air-stable precursors to carbenes used both as organocatalysts or as ligands for transition metal complexes. Traditionally, they are prepared via a multistep synthetic pathway with the low-yielding formation of the triazolium ring occurring in the last step. We have developed an alternative two-step synthesis involving the conversion of a primary amine or aniline derivative to the corresponding 4-substituted triazole followed by a copper-catalyzed arylation with diaryliodonium salts. This transition metal-catalyzed arylation can be carried out under mild conditions in acetonitrile and is tolerant toward both water and oxygen. Additionally, the high functional group tolerance of the protocol described here gives easy access to triazolium salts containing heterocyclic substituents or sulfides.
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spelling pubmed-68222202019-11-01 Catalytic Preparation of 1-Aryl-Substituted 1,2,4-Triazolium Salts Hutchinson, Scott M. Ardón-Muñoz, Luis G. Ratliff, Margarita L. Bolliger, Jeanne L. ACS Omega [Image: see text] 1,4-Diaryl- and 1-aryl-4-alkyl-substituted 1,2,4-triazolium salts are convenient air-stable precursors to carbenes used both as organocatalysts or as ligands for transition metal complexes. Traditionally, they are prepared via a multistep synthetic pathway with the low-yielding formation of the triazolium ring occurring in the last step. We have developed an alternative two-step synthesis involving the conversion of a primary amine or aniline derivative to the corresponding 4-substituted triazole followed by a copper-catalyzed arylation with diaryliodonium salts. This transition metal-catalyzed arylation can be carried out under mild conditions in acetonitrile and is tolerant toward both water and oxygen. Additionally, the high functional group tolerance of the protocol described here gives easy access to triazolium salts containing heterocyclic substituents or sulfides. American Chemical Society 2019-10-18 /pmc/articles/PMC6822220/ /pubmed/31681902 http://dx.doi.org/10.1021/acsomega.9b03109 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Hutchinson, Scott M.
Ardón-Muñoz, Luis G.
Ratliff, Margarita L.
Bolliger, Jeanne L.
Catalytic Preparation of 1-Aryl-Substituted 1,2,4-Triazolium Salts
title Catalytic Preparation of 1-Aryl-Substituted 1,2,4-Triazolium Salts
title_full Catalytic Preparation of 1-Aryl-Substituted 1,2,4-Triazolium Salts
title_fullStr Catalytic Preparation of 1-Aryl-Substituted 1,2,4-Triazolium Salts
title_full_unstemmed Catalytic Preparation of 1-Aryl-Substituted 1,2,4-Triazolium Salts
title_short Catalytic Preparation of 1-Aryl-Substituted 1,2,4-Triazolium Salts
title_sort catalytic preparation of 1-aryl-substituted 1,2,4-triazolium salts
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6822220/
https://www.ncbi.nlm.nih.gov/pubmed/31681902
http://dx.doi.org/10.1021/acsomega.9b03109
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