4,4′,4″-Trimethyl-2,2′:6′,2″-terpyridine by Oxidative Coupling of 4-Picoline

[Image: see text] Alkylated terpyridine ligands are an increasingly important component of catalysis and dyes but are costly because their synthesis is challenging and often low-yielding. We report an improved method for the Pd/C-catalyzed dehydrogenative coupling of 4-picoline to form the bi- and t...

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Autores principales: Robo, Michael T., Prinsell, Michael R., Weix, Daniel J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4227585/
https://www.ncbi.nlm.nih.gov/pubmed/25343728
http://dx.doi.org/10.1021/jo501925s
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author Robo, Michael T.
Prinsell, Michael R.
Weix, Daniel J.
author_facet Robo, Michael T.
Prinsell, Michael R.
Weix, Daniel J.
author_sort Robo, Michael T.
collection PubMed
description [Image: see text] Alkylated terpyridine ligands are an increasingly important component of catalysis and dyes but are costly because their synthesis is challenging and often low-yielding. We report an improved method for the Pd/C-catalyzed dehydrogenative coupling of 4-picoline to form the bi- and terpyridine. The addition of MnO(2) improves the yield of the reaction, making the reaction useful on a large scale (up to 200 mmol). The use of Pd(OAc)(2) or Pd/C/pivalic acid leads to the selective formation of bipyridine.
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spelling pubmed-42275852015-10-24 4,4′,4″-Trimethyl-2,2′:6′,2″-terpyridine by Oxidative Coupling of 4-Picoline Robo, Michael T. Prinsell, Michael R. Weix, Daniel J. J Org Chem [Image: see text] Alkylated terpyridine ligands are an increasingly important component of catalysis and dyes but are costly because their synthesis is challenging and often low-yielding. We report an improved method for the Pd/C-catalyzed dehydrogenative coupling of 4-picoline to form the bi- and terpyridine. The addition of MnO(2) improves the yield of the reaction, making the reaction useful on a large scale (up to 200 mmol). The use of Pd(OAc)(2) or Pd/C/pivalic acid leads to the selective formation of bipyridine. American Chemical Society 2014-10-24 2014-11-07 /pmc/articles/PMC4227585/ /pubmed/25343728 http://dx.doi.org/10.1021/jo501925s 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 Robo, Michael T.
Prinsell, Michael R.
Weix, Daniel J.
4,4′,4″-Trimethyl-2,2′:6′,2″-terpyridine by Oxidative Coupling of 4-Picoline
title 4,4′,4″-Trimethyl-2,2′:6′,2″-terpyridine by Oxidative Coupling of 4-Picoline
title_full 4,4′,4″-Trimethyl-2,2′:6′,2″-terpyridine by Oxidative Coupling of 4-Picoline
title_fullStr 4,4′,4″-Trimethyl-2,2′:6′,2″-terpyridine by Oxidative Coupling of 4-Picoline
title_full_unstemmed 4,4′,4″-Trimethyl-2,2′:6′,2″-terpyridine by Oxidative Coupling of 4-Picoline
title_short 4,4′,4″-Trimethyl-2,2′:6′,2″-terpyridine by Oxidative Coupling of 4-Picoline
title_sort 4,4′,4″-trimethyl-2,2′:6′,2″-terpyridine by oxidative coupling of 4-picoline
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4227585/
https://www.ncbi.nlm.nih.gov/pubmed/25343728
http://dx.doi.org/10.1021/jo501925s
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AT prinsellmichaelr 444trimethyl2262terpyridinebyoxidativecouplingof4picoline
AT weixdanielj 444trimethyl2262terpyridinebyoxidativecouplingof4picoline

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