Synthesis, Table of Contents Synthesis 2013; 45(22): 3099-3102DOI: 10.1055/s-0033-1338520 practical synthetic procedures © Georg Thieme Verlag Stuttgart · New YorkSubstituted 2,2′-Bipyridines by Nickel Catalysis: 4,4′-Di-tert-butyl-2,2′-bipyridine Authors Author Affiliations Joseph A. Buonomo Department of Chemistry, University of Rochester, Rochester, NY 14627-0216, USA, Fax: +1(585)2760205 Email: daniel.weix@rochester.edu Daniel A. Everson Department of Chemistry, University of Rochester, Rochester, NY 14627-0216, USA, Fax: +1(585)2760205 Email: daniel.weix@rochester.edu Daniel J. Weix* Department of Chemistry, University of Rochester, Rochester, NY 14627-0216, USA, Fax: +1(585)2760205 Email: daniel.weix@rochester.edu Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract A simple, ligand-free synthesis of the important bipyridyl ligand 4,4′-di-tert-butyl-2,2′-bipyridine is presented. 5,5′-Bis(trifluoromethyl)-2,2′-bipyridine is also synthesized by the same protocol. The syntheses efficiently couple the parent 2-chloropyridines by a nickel-catalyzed dimerization with manganese powder as the terminal reductant. Key words Key wordsnickel - 4,4′-di-tert-butyl-2,2′-bipyridine - pyridine - catalysis - reductive Full Text References References 1a Marin V, Holder E, Hoogenboom R, Schubert US. Chem. Soc. Rev. 2007; 36: 618 1b Kwong H.-L, Yeung H.-L, Yeung C.-T, Lee W.-S, Lee C.-S, Wong W.-L. Coord. Chem. Rev. 2007; 251: 2188 1c Balzani V, Bergamini G, Marchioni F, Ceroni P. Coord. Chem. Rev. 2006; 250: 1254 2a Ishiyama T, Takagi J, Ishida K, Miyaura N, Anastasi NR, Hartwig JF. J. Am. Chem. Soc. 2001; 124: 390 2b Mkhalid IA. I, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem. Rev. 2010; 110: 890 2c Roosen PC, Kallepalli VA, Chattopadhyay B, Singleton DA, Maleczka RE, Smith MR. J. Am. Chem. Soc. 2012; 134: 11350 3a Everson DA, Shrestha R, Weix DJ. J. Am. Chem. Soc. 2010; 132: 920 3b Everson DA, Jones BA, Weix DJ. J. Am. Chem. Soc. 2012; 134: 6146 3c Wotal AC, Weix DJ. Org. Lett. 2012; 14: 1476 3d Everson DA, George DT, Weix DJ. Org. Synth. 2013; 90: 200 3e Shrestha R, Dorn SC. M, Weix DJ. J. Am. Chem. Soc. 2013; 135: 751 3f Wang S, Qian Q, Gong H. Org. Lett. 2012; 14: 3352 3g Yin H, Zhao C, You H, Lin K, Gong H. Chem. Commun. 2012; 48: 7034 4 Zultanski SL, Fu GC. J. Am. Chem. Soc. 2013; 135: 624 5 Tomashenko OA, Escudero-Adán EC, Martínez Belmonte M, Grushin VV. Angew. Chem. Int. Ed. 2011; 50: 7655 6 Smieja JM, Sampson MD, Grice KA, Benson EE, Froehlich JD, Kubiak CP. Inorg. Chem. 2013; 52: 2484 7a Slinker JD, Gorodetsky AA, Lowry MS, Wang J, Parker S, Rohl R, Bernhard S, Malliaras GG. J. Am. Chem. Soc. 2004; 126: 2763 7b Lowry MS, Hudson WR, Pascal RA, Bernhard S. J. Am. Chem. Soc. 2004; 126: 14129 7c Nagib DA, Scott ME, MacMillan DW. C. J. Am. Chem. Soc. 2009; 131: 10875 7d Nguyen JD, D’Amato EM, Narayanam JM, Stephenson CR. Nat. Chem. 2012; 4: 854 8 Aldrich is the only large commercial supplier listed in the eMolecules or Scifinder databases. Aldrich has been frequently backordered on this ligand since the early spring of 2012, but when it is in stock it is $ 8–10/g. Currently (6/13/13) it is listed as backordered until 7/31/13. Other, smaller, suppliers list prices of > $ 200/g. 9a McGill CK. US Patent 4267335, 1981 ; Chem. Abstr. 1980, 92, 110871. 9b Adams CJ, James SL, Liu X, Raithby PR, Yellowlees LJ. J. Chem. Soc., Dalton Trans. 2000; 63 9c Awad DJ, Schilde U, Strauch P. Inorg. Chim. Acta 2011; 365: 127 10a Badger GM, Sasse WH. F. J. Chem. Soc. 1956; 616 10b Achar S, Scott JD, Vittal JJ, Puddephatt RJ. Organometallics 1992; 12: 4592 10c Belser P, Zelewsky AV. Helv. Chim. Acta 1980; 63: 1675 10d Dai S, Wu Y, Pan X, Shi C, Wang K. Chinese Patent CN1443758 A 20030924, 2003 ; Chem. Abstr. 2005, 143, 326225. 11a Rosevear PE, Sasse WH. F. J. Heterocycl. Chem. 1971; 8: 483 11b Belser P, Zelewsky AV. Helv. Chim. Acta 1980; 63: 1675 11c Ben Hadda T, Le Bozec H. Inorg. Chim. Acta 1993; 204: 103 11d Ref. 10d Selected examples: 12a Peng J, Liu X, Kishi Y. Tetrahedron Lett. 2011; 52: 2172 12b de França KW. R, Navarro M, Léonel É, Durandetti M, Nédélec J.-Y. J. Org. Chem. 2002; 67: 1838 12c Iyoda M, Otsuka H, Sato K, Nisato N, Oda M. Bull. Chem. Soc. Jpn. 1990; 63: 80 Selected examples: 13a Ram RN, Singh V. Tetrahedron Lett. 2006; 47: 7625 13b Kuroboshi M, Waki Y, Tanaka H. J. Org. Chem. 2003; 68: 3938 13c Penalva V, Hassan J, Lavenot L, Gozzi C, Lemaire M. Tetrahedron Lett. 1998; 39: 2559 13d Hassan J, Penalva V, Lavenot L, Gozzi C, Lemaire M. Tetrahedron 1998; 54: 13793 14a Fu R, Bercaw JE, Labinger JA. Organometallics 2011; 30: 6751 14b Vidal Juan B, Forns Berenguel MP, Castillo McQuade M, Erra Sola M, Mir Cepeda M. Patent WO2012041476 (A1), 2012 ; Chem. Abstr. 2012, 156, 4777497. 15 McFarland SA, Lee FS, Cheng KA. W. Y, Cozens FL, Schepp NP. J. Am. Chem. Soc. 2005; 127: 7065 16 Deng JZ, Paone DV, Ginnetti AT, Kurihara H, Dreher SD, Weissman SA, Stauffer SR, Burgey CS. Org. Lett. 2008; 11: 345 17 Chan KS, Tse AK. S. Synth. Commun. 1993; 23: 1929 18a Yamamoto T, Wakabayashi S, Osakada K. J. Organomet. Chem. 1992; 428: 223 18b Osakada K, Yamamoto T. Coord. Chem. Rev. 2000; 198: 379 19 Awad DJ, Schilde U, Strauch P. Inorg. Chim. Acta 2011; 365: 127 20 Kim S.-H, Rieke RD. Tetrahedron 2010; 66: 3135 21 Zeng M, Du Y, Shao L, Qi C, Zhang X.-M. J. Org. Chem. 2010; 75: 2556 Supplementary Material Supplementary Material Supporting Information (PDF) Primary Data Primary Data (ZIP)
