Download PDF
Synthesis 2005(16): 2730-2738  
DOI: 10.1055/s-2005-872119
PAPER
© Georg Thieme Verlag Stuttgart · New York

Cross-Coupling Reaction of Iodo-1,2,3-triazoles Catalyzed by Palladium

Juan Deng, Yong-Ming Wu*, Qing-Yun Chen*
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Rd, Shanghai 200032, P. R. China
Fax: +86(21)64166128; e-Mail: ymwu@mail.sioc.ac.cn ;
Further Information

Publication History

Received 12 April 2005
Publication Date:
04 August 2005 (online)

    Permissions and Reprints All articles of this category

Abstract

The Suzuki, Heck and Sonogashira reactions of 1,4-di­substituted 5-iodo-1,2,3-trizaoles were studied. A versatile method for regioselective synthesis of 1,4,5-trisubstituted-1,2,3-triazoles was developed.

Key Words

Suzuki reaction - Heck reaction - Sonogashira reaction - palladium - 1,2,3-trizaoles

    References

  • 1a Metal-Catalyzed Cross-Coupling Reactions   Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998. 
    Google Scholar
  • 1b Tsuji J. Transition Metal Reagents and Catalysts: Innovation in Organic Synthesis   Wiley; Chichester: 1995. 
    Google Scholar
  • 1c Miyaura N. Top. Curr. Chem.  2002,  219:  1 
    Google Scholar
  • 2a Handbook of Organopalladium Chemistry for Organic Synthesis   Negishi E. Wiley-Interscience; New York: 2002. 
    Google Scholar
  • 2b Tsuji J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century   Wiley; Chichester: 2004. 
    Google Scholar
  • 3a Madin A. O’Donnell CJ. Oh T. Old DW. Overman LE. Sharp MJ. Angew. Chem. Int. Ed.  1999,  38:  2934 
    CrossrefGoogle Scholar
  • 3b Hynes J. Overman LE. Nasser T. Rucker PV. Tetrahedron Lett.  1998,  39:  4647 
    CrossrefGoogle Scholar
  • 3c Hong CY. Overman LE. Romero A. Tetrahedron Lett.  1997,  38:  8439 
    CrossrefGoogle Scholar
  • 4a Wu GG. Wong YS. Poirier M. Org. Lett.  1999,  1:  745 
    CrossrefGoogle Scholar
  • 4b Smith GB. Dezeny GC. Hughes DL. King AO. Verhoeven TR. J. Org. Chem.  1994,  59:  8151 
    CrossrefGoogle Scholar
  • 5a Kadnikov DV. Larock RC. Org. Lett.  2000,  2:  3643 
    CrossrefGoogle Scholar
  • 5b Lopez-Dober MP. Castedo L. Granja JR. Org. Lett.  2001,  3:  2823 
    CrossrefGoogle Scholar
  • 5c Novak Z. Szabo A. Rapasi J. Kotschy A. J. Org. Chem.  2003,  68:  3327 
    CrossrefGoogle Scholar
  • 6 Dakin LA. Langille NF. Panek JS. J. Org. Chem.  2002,  67:  6812 
    CrossrefGoogle Scholar
  • 7 Branu RU. Zeilter K. Muller TJJ. Org. Lett.  2001,  3:  3297 
    CrossrefGoogle Scholar
  • 8 Sarkar A. Okada S. Nakanishi H. Matsuda H. Helv. Chim. Acta  1999,  82:  138 
    CrossrefGoogle Scholar
  • 9 Yue D. Larock RC. J. Org. Chem.  2002,  67:  1905 
    CrossrefPubMedGoogle Scholar
  • 10a Ohta A. Akita Y. Ohkuwa T. Chiba M. Fukunaga R. Miyafuji A. Nakata T. Tani N. Aoyagi Y. Heterocycles  1990,  31:  1951 
    CrossrefGoogle Scholar
  • 10b Aoyagi Y. Inoue A. Koizumi I. Hashimoto R. Tokunaga K. Gohma K. Komatsu J. Sekine K. Miyafuji A. Kunoh J. Honma R. Akita Y. Ohta A. Heterocycles  1992,  33:  257 
    CrossrefGoogle Scholar
  • 11 Gelman D. Tsvelikhovsky D. Molander GA. Blum J. J. Org. Chem.  2002,  67:  6287 
    CrossrefGoogle Scholar
  • 12 Tan JQ. Chang JH. Demg MZ. Chinese J. Chem.  2004,  22:  941 ; Chem. Abstr.  2004,  140:  145997 
    Google Scholar
  • 13 Fan W.-Q. Katritzky AR. In Comprehensive Heterocyclic Chemistry II   Vol. 4:  Katritzky AR. Rees CW. Scriven WV. Elsevier; Oxford: 1996.  p.1-126  
    Google Scholar
  • 14 Alvarez R. Velazquez S. San F. Aquaro S. De C. Perno CF. Karlesson A. Balzarini J. Camarasa MJ. J. Med. Chem.  1994,  37:  4185 
    CrossrefPubMedGoogle Scholar
  • 15 Genin MJ. Allwine DA. Anderson DJ. Barbachyn MR. Emmert DE. Garmon SA. Graber DR. Grega KC. Hester JB. Hutchinson DK. Morris J. Reischer RJ. Ford CW. Zurenco GE. Hamel JC. Schaadt RD. Stapertand D. Yagi BH. J. Med. Chem.  2000,  43:  953 
    CrossrefGoogle Scholar
  • 16 Brockunier LL. Parmee ER. Ok HO. Candelore MR. Cascieri MA. Colwell LF. Deng L. Feeney WP. Forest MJ. Hom GJ. MacIntyre DE. Tota LM. Wyvratt J. Fisher MH. Weber AE. Bioorg. Med. Chem. Lett.  2000,  10:  2111 
    CrossrefGoogle Scholar
  • 17a Katritzky AR. Zhang Y. Singh SK. Heterocycles  2003,  60:  1225 
    CrossrefPubMedGoogle Scholar
  • 17b Gothelf KV. Jørgensen KA. Chem. Rev.  1998,  98:  863 
    CrossrefPubMedGoogle Scholar
  • 18a Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed.  2002,  41:  2596 
    CrossrefGoogle Scholar
  • 18b Tornøe CW. Christensen C. Meldal M. J. Org. Chem.  2002,  67:  3057 
    CrossrefGoogle Scholar
  • 18c Wang Q. Chan TR. Hilgraf R. Fokin VV. Sharpless KB. Finn MG. J. Am. Chem. Soc.  2003,  125:  3192 
    CrossrefGoogle Scholar
  • 18d Lober S. Rodriguez-Loaiza P. Gmeiner P. Org. Lett.  2003,  5:  1753 
    CrossrefGoogle Scholar
  • 18e Pérez-Balderas F. Ortega-Munoz M. Morales-Sanfrutos J. Hernández-Mateo F. Calvo-Flores FG. Calvo-Asín JA. Isac-García J. Santoyo-González F. Org. Lett.  2003,  5:  1951 
    CrossrefGoogle Scholar
  • 18f Krasinski A. Fokin VV. Sharpless KB. Org. Lett.  2004,  6:  1237 
    CrossrefGoogle Scholar
  • 18g Kamijo S. Jin T. Huo Z. Yamamoto Y. J. Am. Chem. Soc.  2003,  125:  7786 
    CrossrefGoogle Scholar
  • 18h Kamijo S. Jin T. Huo Z. Yamamoto Y. J. Org. Chem.  2004,  69:  2386 
    CrossrefGoogle Scholar
  • 18i Appukkuttan P. Dehaen F. Wim VV. Van der Eycken E. Org. Lett.  2004,  6:  4223 
    CrossrefGoogle Scholar
  • 19a Wu YM. Deng J. Fang X. Chen QY. J. Fluorine Chem.  2004,  125:  1415 
    Google Scholar
  • 19b Wu YM. Deng J. Li Y. Chen QY. Synthesis  2005,  in press 
    Google Scholar
  • For reviews see:
  • 20a Suzuki A. J. Organomet. Chem.  1999,  576:  147 
    Google Scholar
  • 20b Miyaura N. In Advances in Metal-Organic Chemistry   Vol. 6:  Liebeskind LS. JAI Press; London: 1998.  p.187-243  
    Google Scholar
  • 20c Suzuki A. In Metal-Catalyzed Cross-Coupling Reactions   Diederich A. Stang PJ. Wiley-VCH; New York: 1998.  Chap. 2.
    Google Scholar
  • 20d Standforth SP. Tetrahedron  1998,  54:  163 
    Google Scholar
  • 20e Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
    Google Scholar
  • For reviews, see:
  • 21a de Meijere A. Meyer FE. Angew. Chem., Int. Ed. Engl.  1994,  33:  2379 
    CrossrefGoogle Scholar
  • 21b de Meijere A. Bräse S. J. Organomet. Chem.  1999,  576:  88 
    CrossrefGoogle Scholar
  • 21c Cacchi S. J. Organomet. Chem.  1999,  576:  111 
    CrossrefGoogle Scholar
  • 21d Negishi E.-i. Copéret C. Ma SM. Liou SY. Liu F. Chem. Rev.  1996,  96:  365 
    CrossrefGoogle Scholar
  • 21e Heck RF. Org. React.  1982,  27:  345 
    CrossrefGoogle Scholar
  • 21f Beletskaya IP. Cheprakov AV. Chem. Rev.  2000,  100:  3009 
    CrossrefGoogle Scholar
  • 21g Whitcombe NJ. Hii KK. Gibson SE. Tetrahedron  2001,  57:  7449 
    CrossrefGoogle Scholar
  • The silver salt effect for enhancing the reaction rate for Heck type reactions has been first reported for the arylation of vinyl and allyl trimethylsilanes:
  • 22a Karabelas K. Hallberg A. Tetrahedron Lett.  1985,  26:  3131 
    Google Scholar
  • 22b Karabelas K. Westerlund C. Hallberg A. J. Org. Chem.  1985,  50:  3896 
    Google Scholar
  • 22c Karabelas K. Hallberg A. J. Org. Chem.  1986,  51:  5286 
    Google Scholar
  • 23a Jeffery T. J. Chem. Soc., Chem. Commun.  1984,  1287 
    CrossrefGoogle Scholar
  • 23b Jeffery T. Tetrahedron Lett.  1985,  26:  2667 
    CrossrefGoogle Scholar
  • 23c Jeffery T. Tetrahedron Lett.  1991,  32:  2121 
    CrossrefGoogle Scholar
  • For reviews, see:
  • 24a Sonogashira K. In Metal-Catalyzed Cross-Coupling Reactions   Diederich F. Stang PJ. Wiley-VCH; New York: 1998.  Chap. 5.
    Google Scholar
  • 24b Brandsma L. Vasilevsky SF. Verkruijsse HD. In Application of Transition Metal Catalysts in Organic Synthesis   Springer; New York: 1998.  Chap. 10.
    Google Scholar
  • 24c Rossi R. Carpita A. Bellina F. Org. Prep. Proced. Int.  1995,  27:  127 
    Google Scholar
  • 24d Sonogashira K. In Comprehensive Organic Synthesis   Vol. 3:  Trost BM. Fleming I. Pergamon; New York: 1991.  Chap. 2.4.
    Google Scholar
  • 24e Negishi E. Anastasia L. Chem. Rev.  2003,  103:  1979 
    Google Scholar