Download PDF
Synthesis 2009(20): 3527-3532  
DOI: 10.1055/s-0029-1216985
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

The Sequential Sonogashira-Click Reaction: A Versatile Route to 4-Aryl-1,2,3-triazoles

Krisztián Lőrincz, Péter Kele, Zoltán Novák*
Department of Organic Chemistry, Institute of Chemistry, Eötvös Loránd University, Pázmány Péter stny. 1/a, 1117 Budapest, Hungary
Fax: +36(1)3722909; e-Mail: novakz@elte.hu;
Further Information

Publication History

Received 5 June 2009
Publication Date:
03 September 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

Aryl halides can be easily transformed in a one-pot procedure into 4-aryl-1,2,3-triazoles with palladium/copper-catalyzed Sonogashira­-click reaction sequence, using trimethylsilylacetylene as acetylene surrogate.

Key words

alkynes - azides - cycloadditions - copper - cross-coupling

    References

  • 1a Negishi E. de Meijere A. Handbook of Organopalladium Chemistry for Organic Synthesis   Wiley; New York: 2002. 
    Google Scholar
  • 1b de Meijere A. Diederich F. Metal-Catalyzed Cross-Coupling Reactions   Wiley-VCH; Weinheim: 2004. 
    Google Scholar
  • 1c Tsuji J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century   Wiley; Chichester: 2004. 
    Google Scholar
  • 1d Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett.  1975,  4467 
    Google Scholar
  • 1e Doucet H. Hierso J.-C. Angew. Chem. Int. Ed.  2007,  46:  834 
    Google Scholar
  • 1f Chinchilla R. Najera C. Chem. Rev.  2007,  107:  874 
    Google Scholar
  • 2a Tørnoe CW. Christensen C. Meldal M. J. Org. Chem.  2002,  67:  3057 
    Google Scholar
  • 2b Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed.  2002,  41:  2596 
    Google Scholar
  • 2c Jones GO. Houk KN. J. Org. Chem.  2008,  73:  1333 
    Google Scholar
  • 2d Kolb HC. Sharpless KB. Drug Discovery Today  2003,  8:  1128 
    Google Scholar
  • 2e Lutz J.-F. Angew. Chem. Int. Ed.  2007,  46:  1018 
    Google Scholar
  • 3 Soheili A. Albaneze-Walker J. Murry JA. Dormer PG. Hughes DL. Org. Lett.  2003,  5:  4191 
    CrossrefPubMedGoogle Scholar
  • 4a Novák Z. Nemes P. Kotschy A. Org. Lett.  2004,  6:  4917 
    Google Scholar
  • 4b Nagy A. Novák Z. Kotschy A. J. Organomet. Chem.  2005,  690:  4453 
    Google Scholar
  • 4c Chow H. Wan C. Low K. Yeung Y. J. Org. Chem.  2001,  66:  1910 
    Google Scholar
  • 5a Csékei M. Novák Z. Kotschy A. Tetrahedron  2008,  64:  975 
    Google Scholar
  • 5b Csékei M. Novák Z. Kotschy A. Tetrahedron  2008,  64:  8992 
    Google Scholar
  • 7 Luo L. Wilhelm C. Sun A. Grey CP. Lauher JW. Goroff NS. J. Am. Chem. Soc.  2008,  130:  7702 
    CrossrefGoogle Scholar
  • 8 Sirion U. Kim HJ. Lee JH. Seo JW. Lee BS. Lee SJ. Oh SJ. Chi DY. Tetrahedron Lett.  2007,  48:  3953 
    CrossrefGoogle Scholar
  • 9 Aldridge WS. Horstein BJ. Serron S. Dattelbaum DL. Schoonover JR. Meyer TJ. J. Org. Chem.  2006,  71:  5186 
    CrossrefGoogle Scholar
6

When TBAF was added before the azide, 9% diphenylbuta-diyne was formed as by-product in the reaction mixture. With the addition of azide before the TBAF, we were able to suppress the homocoupling of the in situ formed terminal acetylene in every tested solvent. In EtOH-CH2Cl2 solvent mixture the amount of the diphenylbutadiyne side product remained below 1%.