Rapid Room‐Temperature, Chemoselective C [Formula: see text] −C [Formula: see text] Coupling of Poly(pseudo)halogenated Arenes Enabled by Palladium(I) Catalysis in Air

While chemoselectivities in Pd(0)‐catalyzed coupling reactions are frequently non‐intuitive and a result of a complex interplay of ligand/catalyst, substrate, and reaction conditions, we herein report a general method based on Pd(I) that allows for an a priori predictable chemoselective C [Formula:...

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Detalles Bibliográficos
Autores principales: Kalvet, Indrek, Magnin, Guillaume, Schoenebeck, Franziska
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5299498/
https://www.ncbi.nlm.nih.gov/pubmed/28032945
http://dx.doi.org/10.1002/anie.201609635
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author Kalvet, Indrek
Magnin, Guillaume
Schoenebeck, Franziska
author_facet Kalvet, Indrek
Magnin, Guillaume
Schoenebeck, Franziska
author_sort Kalvet, Indrek
collection PubMed
description While chemoselectivities in Pd(0)‐catalyzed coupling reactions are frequently non‐intuitive and a result of a complex interplay of ligand/catalyst, substrate, and reaction conditions, we herein report a general method based on Pd(I) that allows for an a priori predictable chemoselective C [Formula: see text] −C [Formula: see text] coupling at C−Br in preference to C−OTf and C−Cl bonds, regardless of the electronic or steric bias of the substrate. The C−C bond formations are extremely rapid (<5 min at RT) and are catalyzed by an air‐ and moisture‐stable Pd(I) dimer under open‐flask conditions.
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spelling pubmed-52994982017-02-22 Rapid Room‐Temperature, Chemoselective C [Formula: see text] −C [Formula: see text] Coupling of Poly(pseudo)halogenated Arenes Enabled by Palladium(I) Catalysis in Air Kalvet, Indrek Magnin, Guillaume Schoenebeck, Franziska Angew Chem Int Ed Engl Communications While chemoselectivities in Pd(0)‐catalyzed coupling reactions are frequently non‐intuitive and a result of a complex interplay of ligand/catalyst, substrate, and reaction conditions, we herein report a general method based on Pd(I) that allows for an a priori predictable chemoselective C [Formula: see text] −C [Formula: see text] coupling at C−Br in preference to C−OTf and C−Cl bonds, regardless of the electronic or steric bias of the substrate. The C−C bond formations are extremely rapid (<5 min at RT) and are catalyzed by an air‐ and moisture‐stable Pd(I) dimer under open‐flask conditions. John Wiley and Sons Inc. 2016-12-29 2017-02-01 /pmc/articles/PMC5299498/ /pubmed/28032945 http://dx.doi.org/10.1002/anie.201609635 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Kalvet, Indrek
Magnin, Guillaume
Schoenebeck, Franziska
Rapid Room‐Temperature, Chemoselective C [Formula: see text] −C [Formula: see text] Coupling of Poly(pseudo)halogenated Arenes Enabled by Palladium(I) Catalysis in Air
title Rapid Room‐Temperature, Chemoselective C [Formula: see text] −C [Formula: see text] Coupling of Poly(pseudo)halogenated Arenes Enabled by Palladium(I) Catalysis in Air
title_full Rapid Room‐Temperature, Chemoselective C [Formula: see text] −C [Formula: see text] Coupling of Poly(pseudo)halogenated Arenes Enabled by Palladium(I) Catalysis in Air
title_fullStr Rapid Room‐Temperature, Chemoselective C [Formula: see text] −C [Formula: see text] Coupling of Poly(pseudo)halogenated Arenes Enabled by Palladium(I) Catalysis in Air
title_full_unstemmed Rapid Room‐Temperature, Chemoselective C [Formula: see text] −C [Formula: see text] Coupling of Poly(pseudo)halogenated Arenes Enabled by Palladium(I) Catalysis in Air
title_short Rapid Room‐Temperature, Chemoselective C [Formula: see text] −C [Formula: see text] Coupling of Poly(pseudo)halogenated Arenes Enabled by Palladium(I) Catalysis in Air
title_sort rapid room‐temperature, chemoselective c [formula: see text] −c [formula: see text] coupling of poly(pseudo)halogenated arenes enabled by palladium(i) catalysis in air
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5299498/
https://www.ncbi.nlm.nih.gov/pubmed/28032945
http://dx.doi.org/10.1002/anie.201609635
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