Synthesis 2013; 45(22): 3099-3102
DOI: 10.1055/s-0033-1338520
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Substituted 2,2′-Bipyridines by Nickel Catalysis: 4,4′-Di-tert-butyl-2,2′-bipyridine

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
› Author Affiliations
Further Information

Publication History

Received: 14 June 2013

Accepted after revision: 17 July 2013

Publication Date:
15 August 2013 (online)


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.

Supporting Information

Primary Data

 
  • 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