Synlett 2013; 24(1): 1-5
DOI: 10.1055/s-0032-1317684
synpacts
© Georg Thieme Verlag Stuttgart · New York

Ketone-Based Transition-Metal-Catalyzed Carbon–Carbon and Carbon– Hydrogen Bond Activation: Exploratory Studies

Guangbin Dong*
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712, USA   Fax: +1(512)4710397   Email: gbdong@cm.utexas.edu
› Author Affiliations
Further Information

Publication History

Received: 12 September 2012

Accepted after revision: 01 November 2012

Publication Date:
27 November 2012 (online)


Dedicated to Professor Barry M. Trost

Abstract

The importance and ubiquity of ketone functional groups in organic synthesis has always been a driving force for discovering new modes of reactivity. Stimulated by the challenges of fused-ring synthesis and ketone alkylation, we summarize here our exploratory studies on ketone-based transition-metal-catalyzed carbon–carbon and carbon–hydrogen bond activation.

 
  • References

  • 1 Modern Carbonyl Chemistry . Otera J. Wiley-VCH; Weinheim: 2000
  • 2 Trost BM. Science (Washington, DC, U.S.) 1991; 254: 1471
  • 3 Xu T, Dong G. Angew. Chem. Int. Ed. 2012; 51: 7567
    • 4a Danheiser RL, Gee SK. J. Org. Chem. 1984; 49: 1672
    • 4b Schiess P, Eberle M, Huys-Francotte M, Wirz J. Tetrahedron Lett. 1984; 25: 2201
  • 5 Huffman MA, Liebeskind LS. J. Am. Chem. Soc. 1991; 113: 2771
    • 6a Kondo T, Taguchi Y, Kaneko Y, Niimi M, Mitsudo T. Angew. Chem. Int. Ed. 2004; 43: 5369
    • 6b Kondo T, Niimi M, Nomura M, Wada K, Mitsudo T. Tetrahedron Lett. 2007; 48: 2837
  • 8 Auvinet A-L, Harrity JP. A. Angew. Chem. Int. Ed. 2011; 50: 2769
  • 9 South MS, Liebeskind LS. J. Am. Chem. Soc. 1984; 106: 4181
    • 10a Murakami M, Itahashi T, Ito Y. J. Am. Chem. Soc. 2002; 124: 13976
    • 10b Murakami M, Ashida S. Chem. Commun. (Cambridge) 2006; 4599
  • 11 Cain D In Carbon-Carbon Bond Formation . Vol. 1. Augustine RL. Marcel Dekker; New York: 1979: 85
  • 12 Smith MB, March J. March’s Advanced Organic Chemistry 2001
    • 13a Stork G, Terrell R, Szmuszkovicz JA. J. Am. Chem. Soc. 1954; 76: 2029
    • 13b Stork G, Landesman H. J. Am. Chem. Soc. 1956; 78: 5128
  • 14 Conia JM, Le Perchec P. Synthesis 1975; 1
  • 15 Kennedy-Smith JJ, Staben ST, Toste FD. J. Am. Chem. Soc. 2004; 126: 4526
  • 16 Chan LY, Kim S, Park Y, Lee PH. J. Org. Chem. 2012; 77: 5239 ; and references cited therein
  • 17 Dénès F, Pérez-Luna A, Chemla F. Chem. Rev. 2010; 110: 2366
    • 18a Pei T, Widenhoefer RA. J. Am. Chem. Soc. 2001; 123: 11290
    • 18b Widenhoefer RA. Pure Appl. Chem. 2004; 76: 671
  • 19 Rodriguez AL, Bunlaksananusorn T, Knochel P. Org. Lett. 2000; 2: 3285
  • 20 Iwahama T, Sakaguchi S, Ishii Y. Chem. Commun. (Cambridge) 2000; 2317

    • For reviews on removable DGs, see:
    • 21a Rousseau G, Breit B. Angew. Chem. Int. Ed. 2011; 50: 2450
    • 21b Tan KL. Nat. Chem. 2012; 4: 253
  • 23 Jun C.-H, Moon CW, Kim Y.-M, Lee H, Lee JH. Tetrahedron Lett. 2002; 43: 4233
  • 24 Wang Z, Reinus BJ, Dong G. J. Am. Chem. Soc. 2012; 134: 13954

    • Aminopyridines have been used in aldehyde carbon–hydrogen bond activation; for seminal work and a review, see:
    • 25a Suggs JW. J. Am. Chem. Soc. 1979; 101: 489
    • 25b Jun C.-H, Moon CW, Lee D.-Y. Chem.–Eur. J. 2002; 8: 2423
  • 26 Nishimura O, Mihara S. J. Agric. Food Chem. 1990; 38: 1038

    • For reviews, see:
    • 27a Zhong C, Shi X. Eur. J. Org. Chem. 2010; 2999
    • 27b Allen AE, MacMillan DW. C. Chem. Sci. 2012; 3: 633