title: 4,4',4"-trimethyl-2,2':6',2"-terpyridine by oxidative coupling of 4-picoline.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627-0216, United States.
authors.forename: Michael T
authors.initials: MT
authors.lastname: Robo
authors.forename: Michael R
authors.initials: MR
authors.lastname: Prinsell
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Weix
mesh_terms: D002384:Catalysis; D017895:Manganese Compounds / Q000737:chemistry; D015394:Molecular Structure; D058451:Oxidative Coupling; D010087:Oxides / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D010847:Picolines / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C519940:4,4',4''-tri-tert-butyl-2,2'-6',2''-terpyridine; D017895:Manganese Compounds; D010087:Oxides; D010847:Picolines; D011725:Pyridines; D010165:Palladium; C027424:manganese oxide