Selective and Serial Suzuki–Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters

[Image: see text] Among cross-coupling reactions, the Suzuki–Miyaura transformation stands out because of its practical advantages, including the commercial availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditi...

Descripción completa

Detalles Bibliográficos
Autores principales: Laulhé, Sébastien, Blackburn, J. Miles, Roizen, Jennifer L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5433267/
https://www.ncbi.nlm.nih.gov/pubmed/27537216
http://dx.doi.org/10.1021/acs.orglett.6b02323
_version_ 1783236816026992640
author Laulhé, Sébastien
Blackburn, J. Miles
Roizen, Jennifer L.
author_facet Laulhé, Sébastien
Blackburn, J. Miles
Roizen, Jennifer L.
author_sort Laulhé, Sébastien
collection PubMed
description [Image: see text] Among cross-coupling reactions, the Suzuki–Miyaura transformation stands out because of its practical advantages, including the commercial availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditions can be used to cross-couple alkyl boronic acids or esters with aryl halides, especially 2-pyridyl halides. Herein, we describe two novel Suzuki–Miyaura protocols that enable selective conversion of polychlorinated aromatics, with a focus on reactions to convert 2,6-dichloropyridines to 2-chloro-6-alkylpyridines or 2-aryl-6-alkylpyridines.
format Online
Article
Text
id pubmed-5433267
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-54332672017-08-18 Selective and Serial Suzuki–Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters Laulhé, Sébastien Blackburn, J. Miles Roizen, Jennifer L. Org Lett [Image: see text] Among cross-coupling reactions, the Suzuki–Miyaura transformation stands out because of its practical advantages, including the commercial availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditions can be used to cross-couple alkyl boronic acids or esters with aryl halides, especially 2-pyridyl halides. Herein, we describe two novel Suzuki–Miyaura protocols that enable selective conversion of polychlorinated aromatics, with a focus on reactions to convert 2,6-dichloropyridines to 2-chloro-6-alkylpyridines or 2-aryl-6-alkylpyridines. American Chemical Society 2016-08-18 2016-09-02 /pmc/articles/PMC5433267/ /pubmed/27537216 http://dx.doi.org/10.1021/acs.orglett.6b02323 Text en Copyright © 2016 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 Laulhé, Sébastien
Blackburn, J. Miles
Roizen, Jennifer L.
Selective and Serial Suzuki–Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters
title Selective and Serial Suzuki–Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters
title_full Selective and Serial Suzuki–Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters
title_fullStr Selective and Serial Suzuki–Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters
title_full_unstemmed Selective and Serial Suzuki–Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters
title_short Selective and Serial Suzuki–Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters
title_sort selective and serial suzuki–miyaura reactions of polychlorinated aromatics with alkyl pinacol boronic esters
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5433267/
https://www.ncbi.nlm.nih.gov/pubmed/27537216
http://dx.doi.org/10.1021/acs.orglett.6b02323
work_keys_str_mv AT laulhesebastien selectiveandserialsuzukimiyaurareactionsofpolychlorinatedaromaticswithalkylpinacolboronicesters
AT blackburnjmiles selectiveandserialsuzukimiyaurareactionsofpolychlorinatedaromaticswithalkylpinacolboronicesters
AT roizenjenniferl selectiveandserialsuzukimiyaurareactionsofpolychlorinatedaromaticswithalkylpinacolboronicesters

Ejemplares similares