Synlett 2013; 24(1): 6-10
DOI: 10.1055/s-0032-1317673
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© Georg Thieme Verlag Stuttgart · New York

Metal-Free Oxidative C(sp 3)–H Bond Couplings as Valuable Synthetic Tools for C–C Bond Formations

Renate Rohlmann
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstr. 40, 48149 Münster, Germany   Fax: +49(251)8333202   Email: olga.garcia@uni-muenster.de
,
Olga García Mancheño*
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstr. 40, 48149 Münster, Germany   Fax: +49(251)8333202   Email: olga.garcia@uni-muenster.de
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Further Information

Publication History

Received: 05 October 2012

Accepted after revision: 24 October 2012

Publication Date:
19 November 2012 (online)

Abstract

Metal-free oxidative methods for the direct functionalization of C(sp 3)–H bonds to form new C–C bonds remain challenging. In this article, previous and recent results, the latter devoted to expanding the scope and synthetic applicability, on these metal-free oxidative C–C coupling reactions are highlighted.

 
  • References

    • 1a Dyker G. Handbook of CH Transformations . Wiley-VCH; Weinheim: 2005
    • 1b For a review on C–H bond functionalization in complex organic synthesis, see: Godula K, Sames D. Science 2006; 312: 67

      For selected recent reviews on cross-dehydrogenative couplings, see:
    • 2a Li C.-J. Acc. Chem. Res. 2009; 42: 335
    • 2b Scheuermann CJ. Chem.–Asian J. 2009; 5: 436
    • 2c Klussmann M, Sureshkumar D. Synthesis 2011; 353
    • 2d Liu C, Zhang H, Shi W, Lei A. Chem. Rev. 2011; 111: 1780
    • 2e Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215

      For some recent mechanistic studies, see refs. 1, 2, and:
    • 3a Boess E, Sureshkumar D, Sud A, Wirtz C, Farès C, Klussmann M. J. Am. Chem. Soc. 2011; 133: 8106
    • 3b Klussmann M. J. Am. Chem. Soc. 2012; 134: 5317
  • 4 Zhang Y, Li C.-J. J. Am. Chem. Soc. 2006; 128: 4242
  • 5 Tsang AS.-K, Todd MH. Tetrahedron Lett. 2009; 50: 1199
  • 6 Ramesh D, Ramulu U, Rajaram S, Prabhakar P, Venkateswarlu Y. Tetrahedron Lett. 2010; 51: 4898
  • 7 Li Z, Li H, Guo X, Cao L, Yu R, Li H, Pan S. Org. Lett. 2008; 10: 803
  • 8 Chua L, Qing F.-L. Chem. Commun. 2010; 46: 6285
  • 9 Pintér Á, Sud A, Sureshkumar D, Klussmann M. Angew. Chem. Int. Ed. 2010; 49: 5004
  • 10 Zhang B, Cui Y, Jiao N. Chem. Commun. 2012; 48: 4498
  • 11 Liu Q, Li Y.-N, Zhang H.-H, Chen B, Tung C.-H, Wu L.-Z. Chem.–Eur. J. 2012; 18: 620
    • 12a Benfatti F, Guiteras Capdevila M, Zoli L, Benedetto E, Cozzi PG. Chem. Commun. 2009; 5919
    • 12b Zhang B, Xiang S.-K, Zhang L.-H, Cui Y, Jiao N. Org. Lett. 2012; 14: 5212

    • For organo- and metal co-catalyzed reactions using peroxides, see:
    • 12c Proline–vanadium system: Sud A, Sureshkumar D, Klussmann M. Chem. Commun. 2009; 3169
    • 12d Jørgensen–Hayashi-type catalyst–copper system: Zhang J, Tiwari B, Xing C, Chen X, Chi YR. Angew. Chem. Int. Ed. 2012; 51: 3649

      For the use of activated olefins with electron-withdrawing groups for the oxidative Morita–Baylis-type reaction, see:
    • 13a Li Z, Bohle DS, Li C.-J. Proc. Natl. Acad. Sci. U.S.A. 2006; 103: 8928
    • 13b For the use of silyl enol ethers, see for example: Sureshkumar D, Sud A, Klussmann M. Synlett 2009; 1558
  • 14 Song C.-X, Cai G.-X, Farrell TR, Jiang Z.-P, Li H, Gan L.-B, Shi Z.-J. Chem. Commun. 2009; 6002
  • 15 Liu H, Cao L, Fossey JS, Deng W.-P. Chem. Commun. 2012; 48: 2674
  • 16 Richter H, Garcίa Mancheño O. Org. Lett. 2011; 13: 6066

    • For previous metal-catalyzed oxidative C(sp 3)−C couplings with these types of oxidants, see:
    • 17a Richter H, Garcίa Mancheño O. Eur. J. Org. Chem. 2010; 4460
    • 17b Richter H, Rohlmann R, Garcίa Mancheño O. Chem.–Eur. J. 2011; 17: 11622
  • 18 Richter H, Garcίa Mancheño O. Angew. Chem. Int. Ed. 2012; 51: 8656