Synlett 2014; 25(2): 233-238
DOI: 10.1055/s-0033-1340151
letter
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Cross-Electrophile Coupling of 2-Chloropyridines with Alkyl Bromides

Daniel A. Everson
Department of Chemistry, University of Rochester, Rochester, NY 14627-0216, USA   Fax: +1(585)2760205   Email: daniel.weix@rochester.edu
,
Joseph A. Buonomo
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: 11 August 2013

Accepted after revision: 16 September 2013

Publication Date:
05 November 2013 (online)


Abstract

The synthesis of 2-alkylated pyridines by the nickel-catalyzed cross-coupling of two electrophiles, a 2-chloropyridine and an alkyl bromide, is described. Compared with our previously published conditions for aryl halides, this method uses a different, more rigid, bathophenanthroline ligand and is conducted at high concentration in N,N-dimethylformamide as solvent. The method displays promising functional group compatibility and the conditions are ­orthogonal to those for the Stille coupling.

Supporting Information

Primary Data

 
  • References

  • 1 Raju SV. N, Purandhar K, Reddy PP, Reddy GM, Reddy LA, Reddy KS, Sreenath K, Mukkanti K, Reddy GS. Org. Process Res. Dev. 2005; 10: 33
  • 2 Turner K. Org. Process Res. Dev. 2009; 13: 381
    • 3a Roughley SD, Jordan AM. J. Med. Chem. 2011; 54: 3451
    • 3b Cooper TW. J, Campbell IB, Macdonald SJ. F. Angew. Chem. Int. Ed. 2010; 49: 8082
    • 3c Dugger RW, Ragan JA, Ripin DH. B. Org. Process Res. Dev. 2005; 9: 253
    • 3d Carey JS, Laffan D, Thomson C, Williams MT. Org. Biomol. Chem. 2006; 4: 2337
    • 3e Laird T. Org. Process Res. Dev. 2006; 10: 851
  • 4 Slagt VF, de Vries AH. M, de Vries JG, Kellogg RM. Org. Process Res. Dev. 2009; 14: 30
  • 5 Dick GR, Knapp DM, Gillis EP, Burke MD. Org. Lett. 2010; 12: 2314
    • 6a Nakamura M, Ito S, Matsuo K, Nakamura E. Synlett 2005; 1794
    • 6b Bourdier T, Huiban M, Huet A, Sobrio F, Fouquet E, Perrio C, Barré L. Synthesis 2008; 978
    • 6c Suzuki M, Sumi K, Koyama H, Siqin Hosoya T, Takashima-Hirano M, Doi H. Chem. Eur. J. 2009; 15: 12489
    • 6d Vechorkin O, Proust V, Hu X. J. Am. Chem. Soc. 2009; 131: 9756
    • 7a Huang Y, Bennett F, Girijavallabhan V, Alvarez C, Chan T.-M, Osterman R, Senior M, Kwong C, Bansal N, George Njoroge F, MacCoss M. Tetrahedron Lett. 2010; 51: 2800
    • 7b Girijavallabhan V, Arasappan A, Bennett F, Huang Y, George Njoroge F, MacCoss M. Tetrahedron Lett. 2010; 51: 2797
    • 7c Joubert N, Pohl R, Klepetářová B, Hocek M. J. Org. Chem. 2007; 72: 6797
    • 8a Johnson S, Drowns M, Tatlock J, Linton A, Gonzalez J, Hoffman R, Jewell T, Patel L, Blazel J, Tang M, Li H. Synlett 2010; 796
    • 8b Fürstner A, Leitner A, Méndez M, Krause H. J. Am. Chem. Soc. 2002; 124: 13856
    • 8c Fürstner A, Leitner A. Angew. Chem. Int. Ed. 2002; 41: 609
    • 8d Hintermann L, Dang TT, Labonne A, Kribber T, Xiao L, Naumov P. Chem. Eur. J. 2009; 15: 7167
    • 9a Hoekstra WJ, Patel HS, Liang X, Blanc J.-BE, Heyer DO, Willson TM, Iannone MA, Kadwell SH, Miller LA, Pearce KH, Simmons CA, Shearin J. J. Med. Chem. 2004; 48: 2243
    • 9b Pompeo M, Froese RD. J, Hadei N, Organ MG. Angew. Chem. Int. Ed. 2012; 51: 11354
    • 9c Hendricks RT, Spencer SR, Blake JF, Fell JB, Fischer JP, Stengel PJ, Leveque VJ. P, LePogam S, Rajyaguru S, Najera I, Josey JA, Swallow S. Bioorg. Med. Chem. Lett. 2009; 19: 410
  • 10 Sherry BD, Fürstner A. Acc. Chem. Res. 2008; 41: 1500
  • 11 Tamao K, Sumitani K, Kumada M. J. Am. Chem. Soc. 1972; 94: 4374
  • 12 Fleury-Brégeot N, Presset M, Beaumard F, Colombel V, Oehlrich D, Rombouts F, Molander GA. J. Org. Chem. 2012; 77: 10399
  • 13 Handbook of Functionalized Organometallics : Applications in Synthesis. Knochel P. Wiley-VCH; Weinheim: 2005
    • 14a Everson DA, Jones BA, Weix DJ. J. Am. Chem. Soc. 2012; 134: 6146
    • 14b Everson DA, Shrestha R, Weix DJ. J. Am. Chem. Soc. 2010; 132: 920
    • 14c Prinsell MR, Everson DA, Weix DJ. Chem. Commun. 2010; 46: 5743
    • 14d Shrestha R, Dorn SC. M, Weix DJ. J. Am. Chem. Soc. 2012; 135: 751
    • 14e Anka-Lufford LL, Prinsell MR, Weix DJ. J. Org. Chem. 2012; 77: 9989
    • 14f Shrestha R, Weix DJ. Org. Lett. 2011; 13: 2766
    • 14g Wotal AC, Weix DJ. Org. Lett. 2012; 14: 1476
    • 14h Everson DA, George DT, Weix DJ. Org. Synth. 2013; 90: 200
  • 16 Yan C.-S, Peng Y, Xu X.-B, Wang Y.-W. Chem. Eur. J. 2012; 18: 6039
  • 17 Amatore M, Gosmini C. Angew. Chem. Int. Ed. 2008; 47: 2089
  • 18 Tanaka H, Kuroboshi M. Curr. Org. Chem. 2004; 8: 1027
  • 19 Braña MF, Morán M, Pérez de Vega MJ, Pita-Romero I. J. Org. Chem. 1996; 61: 1369
    • 20a Trost BM, Cook GR. Tetrahedron Lett. 1996; 37: 7485
    • 20b Sirisoma NS, Johnson CR. Tetrahedron Lett. 1998; 39: 2059
    • 20c Barros MT, Maycock CD, Ventura MR. Tetrahedron Lett. 1999; 40: 557
    • 20d Barros MT, Maycock CD, Ventura MR. J. Chem. Soc., Perkin Trans. 1 2001; 166
    • 20e Lee SJ, Lin W. J. Am. Chem. Soc. 2002; 124: 4554
    • 21a Jones GD, McFarland C, Anderson TJ, Vicic DA. Chem. Commun. 2005; 4211
    • 21b Ciszewski JT, Mikhaylov DY, Holin KV, Kadirov MK, Budnikova YH, Sinyashin O, Vicic DA. Inorg. Chem. 2011; 50: 8630
    • 21c Anderson TJ, Jones GD, Vicic DA. J. Am. Chem. Soc. 2004; 126: 8100
    • 22a Fontana F, Minisci F, Nogueira Barbosa MC, Vismara E. Tetrahedron 1990; 46: 2525
    • 22b O’Hara F, Blackmond DG, Baran PS. J. Am. Chem. Soc. 2013; 135: 12122