N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings

[Image: see text] A series of phosphine-ligated palladium precatalysts based on N-methyl- and N-phenyl-2-aminobiphenyl have been developed. Substitution at the nitrogen center prevents the presence of traces of aminobiphenyls that contain a free −NH(2) group from contaminating cross-coupling product...

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Autores principales: Bruno, Nicholas C., Niljianskul, Nootaree, Buchwald, Stephen L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4017611/
https://www.ncbi.nlm.nih.gov/pubmed/24724692
http://dx.doi.org/10.1021/jo500355k
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author Bruno, Nicholas C.
Niljianskul, Nootaree
Buchwald, Stephen L.
author_facet Bruno, Nicholas C.
Niljianskul, Nootaree
Buchwald, Stephen L.
author_sort Bruno, Nicholas C.
collection PubMed
description [Image: see text] A series of phosphine-ligated palladium precatalysts based on N-methyl- and N-phenyl-2-aminobiphenyl have been developed. Substitution at the nitrogen center prevents the presence of traces of aminobiphenyls that contain a free −NH(2) group from contaminating cross-coupling products. These precatalysts produce N-substituted carbazoles upon activation, which cannot consume starting materials. These precatalysts were efficiently generated from 2-aminobiphenyl with minimal purification and found to be highly effective in Suzuki–Miyaura and C–N cross-coupling reactions.
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spelling pubmed-40176112015-04-11 N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings Bruno, Nicholas C. Niljianskul, Nootaree Buchwald, Stephen L. J Org Chem [Image: see text] A series of phosphine-ligated palladium precatalysts based on N-methyl- and N-phenyl-2-aminobiphenyl have been developed. Substitution at the nitrogen center prevents the presence of traces of aminobiphenyls that contain a free −NH(2) group from contaminating cross-coupling products. These precatalysts produce N-substituted carbazoles upon activation, which cannot consume starting materials. These precatalysts were efficiently generated from 2-aminobiphenyl with minimal purification and found to be highly effective in Suzuki–Miyaura and C–N cross-coupling reactions. American Chemical Society 2014-04-11 2014-05-02 /pmc/articles/PMC4017611/ /pubmed/24724692 http://dx.doi.org/10.1021/jo500355k Text en Copyright © 2014 American Chemical Society
spellingShingle Bruno, Nicholas C.
Niljianskul, Nootaree
Buchwald, Stephen L.
N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings
title N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings
title_full N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings
title_fullStr N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings
title_full_unstemmed N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings
title_short N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings
title_sort n-substituted 2-aminobiphenylpalladium methanesulfonate precatalysts and their use in c–c and c–n cross-couplings
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4017611/
https://www.ncbi.nlm.nih.gov/pubmed/24724692
http://dx.doi.org/10.1021/jo500355k
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