Open Access4,4′,4″-Trimethyl-2,2′:6′,2″-terpyridine by Oxidative Coupling of 4-Picoline
Author(s) -
Michael T. Robo,
Michael R. Prinsell,
Daniel J. Weix
Publication year - 2014
Publication title -
the journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/jo501925s
Subject(s) - terpyridine , pivalic acid , oxidative coupling of methane , catalysis , chemistry , yield (engineering) , coupling reaction , picoline , suzuki reaction , combinatorial chemistry , polymer chemistry , medicinal chemistry , organic chemistry , materials science , pyridine , palladium , metal , metallurgy
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 MnO2 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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