Rational Ligand Design for the Arylation of Hindered Primary Amines Guided by Reaction Progress Kinetic Analysis

[Image: see text] We report the Pd-catalyzed arylation of very hindered α,α,α-trisubstituted primary amines. Kinetics-based mechanistic analysis and rational design have led to the development of two biarylphosphine ligands that allow the transformation to proceed with excellent efficiency. The proc...

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Autores principales: Ruiz-Castillo, Paula, Blackmond, Donna G., Buchwald, Stephen L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4379963/
https://www.ncbi.nlm.nih.gov/pubmed/25651374
http://dx.doi.org/10.1021/ja512903g
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author Ruiz-Castillo, Paula
Blackmond, Donna G.
Buchwald, Stephen L.
author_facet Ruiz-Castillo, Paula
Blackmond, Donna G.
Buchwald, Stephen L.
author_sort Ruiz-Castillo, Paula
collection PubMed
description [Image: see text] We report the Pd-catalyzed arylation of very hindered α,α,α-trisubstituted primary amines. Kinetics-based mechanistic analysis and rational design have led to the development of two biarylphosphine ligands that allow the transformation to proceed with excellent efficiency. The process was effective in coupling a wide range of functionalized aryl and heteroaryl halides under mild conditions.
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spelling pubmed-43799632015-04-03 Rational Ligand Design for the Arylation of Hindered Primary Amines Guided by Reaction Progress Kinetic Analysis Ruiz-Castillo, Paula Blackmond, Donna G. Buchwald, Stephen L. J Am Chem Soc [Image: see text] We report the Pd-catalyzed arylation of very hindered α,α,α-trisubstituted primary amines. Kinetics-based mechanistic analysis and rational design have led to the development of two biarylphosphine ligands that allow the transformation to proceed with excellent efficiency. The process was effective in coupling a wide range of functionalized aryl and heteroaryl halides under mild conditions. American Chemical Society 2015-02-04 2015-03-04 /pmc/articles/PMC4379963/ /pubmed/25651374 http://dx.doi.org/10.1021/ja512903g Text en Copyright © 2015 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 Ruiz-Castillo, Paula
Blackmond, Donna G.
Buchwald, Stephen L.
Rational Ligand Design for the Arylation of Hindered Primary Amines Guided by Reaction Progress Kinetic Analysis
title Rational Ligand Design for the Arylation of Hindered Primary Amines Guided by Reaction Progress Kinetic Analysis
title_full Rational Ligand Design for the Arylation of Hindered Primary Amines Guided by Reaction Progress Kinetic Analysis
title_fullStr Rational Ligand Design for the Arylation of Hindered Primary Amines Guided by Reaction Progress Kinetic Analysis
title_full_unstemmed Rational Ligand Design for the Arylation of Hindered Primary Amines Guided by Reaction Progress Kinetic Analysis
title_short Rational Ligand Design for the Arylation of Hindered Primary Amines Guided by Reaction Progress Kinetic Analysis
title_sort rational ligand design for the arylation of hindered primary amines guided by reaction progress kinetic analysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4379963/
https://www.ncbi.nlm.nih.gov/pubmed/25651374
http://dx.doi.org/10.1021/ja512903g
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