Palladium-Catalyzed Amination of Aryl Chlorides and Bromides with Ammonium Salts

[Image: see text] We report the palladium-catalyzed coupling of aryl halides with ammonia and gaseous amines as their ammonium salts. The coupling of aryl chlorides and ortho-substituted aryl bromides with ammonium sulfate forms anilines with higher selectivity for the primary arylamine over the dia...

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Autores principales: Green, Rebecca A., Hartwig, John F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4260968/
https://www.ncbi.nlm.nih.gov/pubmed/25133675
http://dx.doi.org/10.1021/ol501739g
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author Green, Rebecca A.
Hartwig, John F.
author_facet Green, Rebecca A.
Hartwig, John F.
author_sort Green, Rebecca A.
collection PubMed
description [Image: see text] We report the palladium-catalyzed coupling of aryl halides with ammonia and gaseous amines as their ammonium salts. The coupling of aryl chlorides and ortho-substituted aryl bromides with ammonium sulfate forms anilines with higher selectivity for the primary arylamine over the diarylamine than couplings with ammonia in dioxane. The resting state for the reactions of aryl chlorides is different from the resting state for the reactions of aryl bromides, and this change in resting states is proposed to account for a difference in selectivities for reactions of the two haloarenes.
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spelling pubmed-42609682015-04-05 Palladium-Catalyzed Amination of Aryl Chlorides and Bromides with Ammonium Salts Green, Rebecca A. Hartwig, John F. Org Lett [Image: see text] We report the palladium-catalyzed coupling of aryl halides with ammonia and gaseous amines as their ammonium salts. The coupling of aryl chlorides and ortho-substituted aryl bromides with ammonium sulfate forms anilines with higher selectivity for the primary arylamine over the diarylamine than couplings with ammonia in dioxane. The resting state for the reactions of aryl chlorides is different from the resting state for the reactions of aryl bromides, and this change in resting states is proposed to account for a difference in selectivities for reactions of the two haloarenes. American Chemical Society 2014-08-18 2014-09-05 /pmc/articles/PMC4260968/ /pubmed/25133675 http://dx.doi.org/10.1021/ol501739g Text en Copyright © 2014 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 Green, Rebecca A.
Hartwig, John F.
Palladium-Catalyzed Amination of Aryl Chlorides and Bromides with Ammonium Salts
title Palladium-Catalyzed Amination of Aryl Chlorides and Bromides with Ammonium Salts
title_full Palladium-Catalyzed Amination of Aryl Chlorides and Bromides with Ammonium Salts
title_fullStr Palladium-Catalyzed Amination of Aryl Chlorides and Bromides with Ammonium Salts
title_full_unstemmed Palladium-Catalyzed Amination of Aryl Chlorides and Bromides with Ammonium Salts
title_short Palladium-Catalyzed Amination of Aryl Chlorides and Bromides with Ammonium Salts
title_sort palladium-catalyzed amination of aryl chlorides and bromides with ammonium salts
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4260968/
https://www.ncbi.nlm.nih.gov/pubmed/25133675
http://dx.doi.org/10.1021/ol501739g
work_keys_str_mv AT greenrebeccaa palladiumcatalyzedaminationofarylchloridesandbromideswithammoniumsalts
AT hartwigjohnf palladiumcatalyzedaminationofarylchloridesandbromideswithammoniumsalts

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