PDF herunterladen
Synthesis 2012(5): 677-685  
DOI: 10.1055/s-0031-1289697
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Transition-Metal-Catalyzed Synthesis of Aromatic Ketones via Direct C-H Bond Activation

Changduo Pana, Xiaofei Jiab, Jiang Cheng*b
a Wenzhou Institute of Industry & Science, Wenzhou 325000, P. R. of China
b College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325000, P. R. of China
Fax: +86)(577)56998939; e-Mail: jiangcheng@wzu.edu.cn;
Weitere Informationen

Publikationsverlauf

Received 2 November 2011
Publikationsdatum:
13. Februar 2012 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

There are several alternative methods to Friedel-Crafts acylation for the synthesis of ketones. Among these methods, transition-metal-catalyzed acylation of arenes via C-H bond cleavage represents a direct and promising approach to access ketones, in view of the advantages of C-H bond activation; recent advances in the development of this area are summarized.

1 Introduction

2 Acylation of sp² C-H Bonds with Aldehydes via C-H Bond Cleavage

3 Acylation of Arenes with α-Oxocarboxylic Acids via Decarboxylation and C-H Bond Cleavage

4 Acylation of sp² C-H Bonds with α,β-Unsaturated Carboxylic Acids

5 Acylation of sp² C-H Bonds with Acyl Chlorides

6 Summary

Key words

acylation - transition metals - arenes - ketones - C-H bond functionalization

    References

  • 1a Surburg H. Panten J. Common Fragrance and Flavor Materials   5th ed.:  Wiley-VCH; Weinheim: 2006. 
    Suche in Google Scholar
  • 1b Rahimipour S. Palivan C. Barbosa F. Bilkis I. Koch Y. Weiner L. Fridkin M. Mazur Y. Gescheidt G. J. Am. Chem. Soc.  2003,  125:  1376 
    Suche in Google Scholar
  • 1c Van de Putte M. Roskams T. Vandenheede JR. Agostinis P. deWitte PAM. Br. J. Cancer  2005,  92:  1406 
    Suche in Google Scholar
  • 1d Deng Y. Chin Y.-W. Chai H. Keller WJ. Kinghorn AD. J. Nat. Prod.  2007,  70:  2049 
    Suche in Google Scholar
  • 1e Nishizuka Y. Nature  1988,  334:  661 
    Suche in Google Scholar
  • 1f Ding X.-Q. Lindstrom E. Hakanson R. Pharmacol. Toxicol.  1997,  81:  232 
    Suche in Google Scholar
  • 1g Masson PJ. Coup D. Millet J. Brown NL. J. Biol. Chem.  1995,  270:  2662 
    Suche in Google Scholar
  • 1h Prince AM. Pascual D. Meruelo D. Liebes L. Mazur Y. Dubovi E. Mandel M. Lavie G. Photochem. Photobiol.  2000,  71:  188 
    Suche in Google Scholar
  • 2 Olah GA. Friedel-Crafts Chemistry   Wiley; New York: 1973. 
  • 3a Hudlicky M. Oxidation in Organic Chemistry   American Chemical Society; Washington DC: 1990. 
  • 3b Tojo G. Fernandez M. In Oxidation of Alcohols to Aldehyde and Ketones: A Guide to Current Common Practice   Tojo G. Springer; New York: 2006. 
  • 4a Larock RC. Comprehensive Organic Transformations   VCH; New York: 1989.  p.685 
  • 4b March J. Advanced Organic Chemistry   3rd ed.:  Wiley; New York: 1985.  p.433-435 and 824-827  
    Suche in Google Scholar
  • 5a Park YJ. Park J.-W. Jun C.-H. Acc. Chem. Res.  2008,  41:  222 
    Suche in Google Scholar
  • 5b Willis MC. Chem. Rev.  2010,  110:  725 
    Suche in Google Scholar
  • 5c Shibata Y. Tanaka K. J. Am. Chem. Soc.  2009,  131:  12552 
    Suche in Google Scholar
  • 5d Coulter MM. Kou KGM. Galligan B. Dong VM. J. Am. Chem. Soc.  2010,  132:  16330 
    Suche in Google Scholar
  • 5e Phan DHT. Kou KGM. Dong VM. J. Am. Chem. Soc.  2010,  132:  16354 
    Suche in Google Scholar
  • 5f Zhang H.-J. Bolm C. Org. Lett.  2011,  13:  3900 
    Suche in Google Scholar
  • 6a Ruan J. Xiao J. Acc. Chem. Res.  2011,  44:  614 
    Suche in Google Scholar
  • 6b Huang Y.-C. Majumdar KK. Cheng C.-H. J. Org. Chem.  2002,  67:  1682 
    Suche in Google Scholar
  • 6c Shukla P. Cheng C.-H. Org. Lett.  2006,  8:  2867 
    Suche in Google Scholar
  • 6d Ko S. Kang B. Chang S. Angew. Chem. Int. Ed.  2005,  44:  455 
    Suche in Google Scholar
  • 6e Colbon P. Ruan J. Purdie M. Xiao J. Org. Lett.  2010,  12:  3670 
    Suche in Google Scholar
  • 6f Ruan J. Saidi O. Iggo JA. Xiao J. J. Am. Chem. Soc.  2008,  130:  10510 
    Suche in Google Scholar
  • 6g Adak L. Bhadra S. Ranu BC. Tetrahedron Lett.  2010,  51:  3811 
    Suche in Google Scholar
  • 6h Liu Y. Yao B. Deng C.-L. Tang R.-Y. Zhang X.-G. Li J.-H. Org. Lett.  2011,  13:  2184 
    Suche in Google Scholar
  • 6i Colbon P. Ruan J. Purdie M. Mulholland K. Xiao J. Org. Lett.  2011,  13:  5456 
    Suche in Google Scholar
  • 7a Wu X.-F. Neumann H. Beller M. Chem. Soc. Rev.  2011,  40:  4986 
    Suche in Google Scholar
  • 7b Brunet J.-J. Chauvin R. Chem. Soc. Rev.  1995,  24:  89 
    Suche in Google Scholar
  • 8a Pucheault M. Darses S. Genet J.-P. J. Am. Chem. Soc.  2004,  126:  15356 
    Suche in Google Scholar
  • 8b Chuzel O. Roesch A. Genet J.-P. Darses S. J. Org. Chem.  2008,  73:  7800 
    Suche in Google Scholar
  • 8c Qin C. Chen J. Wu H. Cheng J. Zhang Q. Zuo B. Su W. Ding J. Tetrahedron Lett.  2008,  49:  1884 
    Suche in Google Scholar
  • 8d Zheng H. Ding J. Chen J. Liu M. Gao W. Wu H. Synlett  2011,  1626 
  • 8e Li H. Xu Y. Shi E. Wei W. Suo X. Wan X. Chem. Commun.  2011,  47:  7880 
    Suche in Google Scholar
  • 8f Liao Y.-X. Hu Q.-S. J. Org. Chem.  2010,  75:  6986 
    Suche in Google Scholar
  • 8g Weng F. Wang C. Xu B. Tetrahedron Lett.  2010,  51:  2593 
    Suche in Google Scholar
  • 8h Karthikeyan J. Parthasarathy K. Cheng C.-H. Chem. Commun.  2011,  47:  10461 
    Suche in Google Scholar
  • 8i Liu T.-P. Liao Y.-X. Xing C.-H. Hu Q.-S. Org. Lett.  2011,  13:  2452 
    Suche in Google Scholar
  • 9a Alberico D. Scott ME. Lautens M. Chem. Rev.  2007,  107:  174 
    Suche in Google Scholar
  • 9b Lyons W. Sanford MS. Chem. Rev.  2010,  110:  1147 
    Suche in Google Scholar
  • 9c Yeung CS. Dong VM. Chem. Rev.  2011,  111:  1215 
    Suche in Google Scholar
  • 9d Mkhalid IA. Barnard JH. Marder TB. Murphy JM. Hartwig JF. Chem. Rev.  2010,  110:  890 
    Suche in Google Scholar
  • 9e Colby DA. Bergman RG. Ellman JA. Chem. Rev.  2010,  110:  624 
    Suche in Google Scholar
  • 9f Ackermann L. Chem. Rev.  2011,  111:  1315 
    Suche in Google Scholar
  • 9g Ashenhurst JA. Chem. Soc. Rev.  2010,  39:  540 
    Suche in Google Scholar
  • 9h Sun C.-L. Li B.-J. Shi Z.-J. Chem. Commun.  2010,  46:  677 
    Suche in Google Scholar
  • 9i Cho S. Kim J. Kwak J. Chang S. Chem. Soc. Rev.  2011,  40:  5068 
    Suche in Google Scholar
  • 9j Daugulis O. Top. Curr. Chem.  2010,  292:  57 
    Suche in Google Scholar
  • 9k Hirano K. Miura M. Synlett  2011,  294 
  • 10 Chatani N. Directed Metallation, In Topics In Organometallic Chemistry   Vol. 24:  Springer; Berlin: 2008. 
    Suche in Google Scholar
  • 11 Jia X. Zhang S. Wang W. Luo F. Cheng J. Org. Lett.  2009,  11:  3120 
    Suche in Google Scholar
  • 12 Baslé O. Bidange J. Shuai Q. Li C.-J. Adv. Synth. Catal.  2010,  352:  1145 
    Suche in Google Scholar
  • 13 Xiao F. Shuai Q. Zhao F. Baslé O. Deng G. Li C.-J. Org. Lett.  2011,  13:  1614 
    Suche in Google Scholar
  • 14 Chan C.-W. Zhou Z. Chan ASC. Yu W.-Y. Org. Lett.  2010,  12:  3926 
    Suche in Google Scholar
  • 15 Li C. Wang L. Li P. Zhou W. Chem. Eur. J.  2011,  17:  10208 
    Suche in Google Scholar
  • 16 Wu Y. Li B. Mao F. Li X. Kwong FY. Org. Lett.  2011,  13:  3528 
    Suche in Google Scholar
  • 17 Chan C.-W. Zhou Z. Yu W.-Y. Adv. Synth. Catal.  2011,  353:  2999 
    Suche in Google Scholar
  • 18 Yuan Y. Chen D. Wang X. Adv. Synth. Catal.  2011,  353:  3373 
    Suche in Google Scholar
  • 19 Park J. Park E. Kim A. Lee Y. Chi K.-W. Kwak J. Jung Y. Kim I. Org. Lett.  2011,  13:  4390 
    Suche in Google Scholar
  • 20 Sadana AK. Saini RK. Billups WE. Chem. Rev.  2003,  103:  1539 
    Suche in Google Scholar
  • 21 Aidhen IS. Ahuja JR. Tetrahedron Lett.  1992,  33:  5431 
    Suche in Google Scholar
  • 22 Hamura T. Ibusuki Y. Sato K. Matsumoto T. Osamura Y. Suzuki K. Org. Lett.  2003,  5:  3551 
    Suche in Google Scholar
  • 23 Álvarez-Bercedo P. Flores-Gaspar A. Correa A. Martin R. J. Am. Chem. Soc.  2010,  132:  466 
    Suche in Google Scholar
  • 24 Tang B. Song R. Wu C. Liu Y. Zhou M. Wei W. Deng G. Yin D. Li J.-H. J. Am. Chem. Soc.  2010,  132:  8900 
    Suche in Google Scholar
  • 25a Sumpter WC. Chem. Rev.  1944,  34:  393 
    Suche in Google Scholar
  • 25b da Silva JM. Garden SJ. Pinto AC. J. Braz. Chem. Soc.  2001,  12:  273 
    Suche in Google Scholar
  • 26 Rodriguez N. Goossen LJ. Chem. Soc. Rev.  2011,  40:  5030 
    Suche in Google Scholar
  • 27a Goossen LJ. Zimmermann B. Knauber T. Angew. Chem. Int. Ed.  2008,  47:  7103 
    Suche in Google Scholar
  • 27b Goossen LJ. Rudolphi F. Oppel C. Rodriguez N. Angew. Chem. Int. Ed.  2008,  47:  3043 
    Suche in Google Scholar
  • 28 Li M. Wang C. Ge H. Org. Lett.  2011,  13:  2062 
    Suche in Google Scholar
  • 29 Li M. Ge H. Org. Lett.  2010,  12:  3464 
    Suche in Google Scholar
  • 30 Fang P. Li M. Ge H. J. Am. Chem. Soc.  2010,  132:  11898 
    Suche in Google Scholar
  • 31 Yang Y. Chen L. Zhang Z. Zhang Y. Org. Lett.  2011,  13:  1342 
    Suche in Google Scholar
  • 32 Kochi T. Tazawa A. Honda K. Kakiuchi F. Chem. Lett.  2011,  40:  1018 
    Suche in Google Scholar