Download PDF
Synlett 2012(2): 159-162  
DOI: 10.1055/s-0031-1290117
SYNPACTS
© Georg Thieme Verlag Stuttgart ˙ New York

Oxidative Coupling of Tertiary Amines: Scope, Mechanism and Challenges

Kevin M. Jones, Martin Klussmann*
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
Fax: +49(208)3062987; e-Mail: Klusi@mpi-muelheim.mpg.de;
Further Information

Publication History

Received 25 October 2011
Publication Date:
22 December 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

This article highlights the current scope of oxidative coupling reactions of tertiary amines. Emphasis has been placed on recent synthetic and mechanistic studies and suggests potential areas of improvement for the future.

Key words

oxidation - cross-coupling - catalysis - mechanism - C-H functionalization

    References

  • 1a Bergman RG. Nature (London)  2007,  446:  391 
    Google Scholar
  • 1b Labinger JA. Bercaw JE. Nature (London)  2002,  417:  507 
    Google Scholar
  • 1c Readers are also directed to the special ‘C-H Activation’ issue of: Chem. Rev.  2010,  110:  575 
    Google Scholar
  • 2a Colby DA. Bergman RG. Ellman JA. Chem. Rev.  2009,  110:  624 
    Google Scholar
  • 2b Lyons TW. Sanford MS. Chem. Rev.  2010,  110:  1147 
    Google Scholar
  • 3 Zhenyang L. Coord. Chem. Rev.  2007,  251:  2280 
    Google Scholar
  • 4 Doyle MP. Duffy R. Ratnikov M. Zhou L. Chem. Rev.  2009,  110:  704 
    Google Scholar
  • 5a Yeung CS. Dong VM. Chem. Rev.  2011,  111:  1215 
    Google Scholar
  • 5b Scheuermann CJ. Chem. Eur. J.  2010,  5:  436 
    Google Scholar
  • 5c Klussmann M. Sureshkumar D. Synthesis  2011,  353 
    Google Scholar
  • 6a Murahashi S.-I. Komiya N. Terai H. Nakae T. J. Am. Chem. Soc.  2003,  125:  15312 
    Google Scholar
  • 6b Murahashi S.-I. Komiya N. Terai H. Angew. Chem. Int. Ed.  2005,  44:  6931 
    Google Scholar
  • 6c Murahashi S.-I. Nakae T. Terai H. Komiya N. J. Am. Chem. Soc.  2008,  130:  11005 
    Google Scholar
  • For earlier examples also, see:
  • 7a Santamaria J. Herlem D. Khuong-Huu F. Tetrahedron  1977,  33:  2389 
    Google Scholar
  • 7b Chiba T. Takata Y. J. Org. Chem.  1977,  42:  2973 
    Google Scholar
  • 7c Murata S. Teramoto K. Miura M. Nomura M. Bull. Chem. Soc. Jpn.  1993,  66:  1297 
    Google Scholar
  • 8 Li Z. Li C.-J. J. Am. Chem. Soc.  2005,  127:  6968 
    Google Scholar
  • 9 Li Z. Bohle DS. Li C.-J. Proc. Natl. Acad. Sci. U.S.A.  2006,  103:  8928 
    Google Scholar
  • 10 Li Z. Li C.-J. J. Am. Chem. Soc.  2004,  126:  11810 
    Google Scholar
  • 11 Li Z. Li C.-J. J. Am. Chem. Soc.  2005,  127:  3672 
    Google Scholar
  • 12 Li Z. Li C.-J. Eur. J. Org. Chem.  2005,  3173 
    Google Scholar
  • 13a Li Z. Li C.-J. Org. Lett.  2004,  6:  4997 
    Google Scholar
  • 13b Li Z. MacLeod PD. Li C.-J. Tetrahedron: Asymmetry  2006,  17:  590 
    Google Scholar
  • 14 Sureshkumar D. Sud A. Klussmann M. Synlett  2009,  1558 
    Google Scholar
  • 15 Boess E. Sureshkumar D. Sud A. Wirtz C. Farès C. Klussmann M. J. Am. Chem. Soc.  2011,  133:  8106 
    Google Scholar
  • 16 Condie AG. González-Gómez JC. Stephenson CRJ. J. Am. Chem. Soc.  2010,  132:  1464 
    Google Scholar
  • 17 Rueping M. Vila C. Koenigs RM. Poscharny K. Fabry DC. Chem. Commun.  2011,  47:  2360 
    Google Scholar
  • For additional photochemical methods, see:
  • 18a Hari DP. König B. Org. Lett.  2011,  13:  3852 
    Google Scholar
  • 18b Pan Y. Wang S. Kee CW. Dubuisson E. Yang Y. Loh KP. Tan C.-H. Green Chem.  2011, DOI: 10.1039/C1GC15865A
    Google Scholar
  • 19 Zhao L. Li C.-J. Angew. Chem. Int. Ed.  2008,  47:  7075 
    Google Scholar
  • 20 Yang F. Li J. Xie J. Huang Z.-Z. Org. Lett.  2010,  12:  5214 
    Google Scholar
  • 21 Zhang G. Zhang Y. Wang R. Angew. Chem. Int. Ed.  2011,  50:  10429 
    Google Scholar
  • 22 Sundberg RJ. Théret M.-H. Wright L. Org. Prep. Proced. Int.  1994,  26:  386 
    Google Scholar
  • 23 Pandey G. Rani KS. Lakshmaiah G. Tetrahedron Lett.  1992,  33:  5107 
    Google Scholar
  • 24 Niu M. Yin Z. Fu H. Jiang Y. Zhao Y. J. Org. Chem.  2008,  73:  3961 
    Google Scholar
  • 25 Xu X. Li X. Org. Lett.  2009,  11:  1027 
    Google Scholar
  • 26 Daniels MH. Hubbs J. Tetrahedron Lett.  2011,  52:  3543 
    Google Scholar
  • 27 Ohta M. Quick MP. Yamaguchi J. Wünsch B. Itami K. Chem. Eur. J.  2009,  4:  1416 
    Google Scholar
  • 28 Kumaraswamy G. Murthy AN. Pitchaiah A. J. Org. Chem.  2010,  75:  3916 
    Google Scholar
  • 29 Chu L. Zhang X. Qing F.-L. Org. Lett.  2009,  11:  2197 
    Google Scholar
  • 30a Chu L. Qing F.-L. Chem. Commun.  2010,  46:  6285 
    Google Scholar
  • 30b Mitsudera H. Li C.-J. Tetrahedron Lett.  2011,  52:  1898 
    Google Scholar
  • 31 Sud A. Sureshkumar D. Klussmann M. Chem. Commun.  2009,  3169 
    Google Scholar
  • 32 Jones KM. Klussmann M. ChemCatChem  2011,  in press; DOI: 10.1002/cctc.201100324
    Google Scholar
  • 33 Ghobrial M. Schnürch M. Mihovilovic MD. J. Org. Chem.  2011,  76:  8781 
    Google Scholar
  • 34 An example of an iminium ion formed in a metal-free procedure has been reported: Tsang AS.-K. Jensen P. Hook JM. Hashmi ASK. Todd MH. Pure Appl. Chem.  2011,  83:  655 
    Google Scholar
35

An example has been reported, see ref. 17.