Download PDF
Synthesis 2010(14): 2399-2406  
DOI: 10.1055/s-0029-1218776
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Suzuki and Sonogashira Cross-Coupling Reactions in Water Medium with a Reusable Poly(N-vinylcarbazole)-Anchored Palladium(II) Complex

Manirul Islam*a, Paramita Mondala, Anupam Singha Roya, Kazi Tuhina b
a Department of Chemistry, University of Kalyani, Kalyani 741235, WB, India
b Department of Chemistry, Bankim Sadar College, South 24 Paraganas, Tangrakhali 743329, WB, India
e-Mail: manir65@rediffmail.com;
Further Information

Publication History

Received 1 February 2010
Publication Date:
05 May 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

Poly(3,6-dibenzaldimino-N-vinylcarbazole)-anchored palladium(II) complex has been synthesized and characterized by different physicochemical and spectroscopic techniques. The present complex shows excellent catalytic activities for Suzuki and Sonogashira coupling reactions under phosphine-free and copper-free reaction conditions in water medium. This immobilized catalyst can be easily separated and reused for further reactions for more than five times without noticeable loss in the catalytic activity.

Key words

heterogeneous catalysis - Schiff base - palladium complex - cross-coupling - biaryls

    References

  • 1a Stetter J. Lieb F. Angew. Chem. Int. Ed.  2000,  39:  1724 
    Google Scholar
  • 1b Negishi E. Anastasia L. Chem. Rev.  2003,  103:  1979 
    Google Scholar
  • 1c Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed.  2005,  44:  4442 
    Google Scholar
  • 2a Chinchilla R. Nájera C. Chem. Rev.  2007,  107:  874 
    Google Scholar
  • 2b Nicolaou KC. Boddy CNC. Brase S. Winssinger N. Angew. Chem. Int. Ed.  1999,  38:  2096 
    Google Scholar
  • 2c Baudoin O. Cesario M. Guenard D. Gueritte F. J. Org. Chem.  2002,  67:  1199 
    Google Scholar
  • 2d Tsuji J. Palladium Reagents and Catalysts   Wiley; New York: 1995. 
    Google Scholar
  • 2e Paterson I. Davies RDM. Marquez R. Angew. Chem. Int. Ed.  2001,  40:  603 
    Google Scholar
  • 2f Mongin O. Porres L. Moreaux L. Mertz J. Blanchard-Desce M. Org. Lett.  2002,  4:  719 
    Google Scholar
  • 3a Shaughnessy KH. Eur. J. Org. Chem.  2006,  1827 
    Google Scholar
  • 3b Li CJ. Chem. Rev.  1993,  93:  2023 
    Google Scholar
  • 3c Li CJ. Chem. Rev.  2005,  105:  3095 
    Google Scholar
  • 3d Guan JT. Weng TQ. Yu G. Liu SH. Tetrahedron Lett.  2007,  48:  7129 
    Google Scholar
  • 3e Wan Y. Wang H. Zhao Q. Klingstedt M. Terasaki O. Zhao D. J. Am. Chem. Soc.  2009,  131:  4541 
    Google Scholar
  • 4a Zhao FY. Bhanage BM. Shirai M. Arai M. J. Mol. Catal. A: Chem.  1999,  142:  383 
    Google Scholar
  • 4b Reetz MT. de Vries JG. Chem. Commun.  2004,  1559 
    Google Scholar
  • 4c Komáromi A. Tolnai GL. Novák Z. Tetrahedron Lett.  2008,  49:  7294 
    Google Scholar
  • 4d Bakherad M. Keivanloo A. Bahramian B. Hashemi M. Tetrahedron Lett.  2009,  50:  1557 
    Google Scholar
  • 5a Mora M. Jiménez-Sanchidrián C. Ruiz JR. J. Mol. Catal. A: Chem.  2008,  285:  79 
    Google Scholar
  • 5b Shimizu K. Maruyama R. Komai S. Kodama T. Kitayama Y. J. Catal.  2004,  227:  202 
    Google Scholar
  • 5c Reddy EA. Barange DK. Islam A. Mukkanti V. Pal M. Tetrahedron.  2008,  64:  7143 
    Google Scholar
  • 5d Jana S. Dutta B. Bera R. Koner S. Inorg. Chem.  2008,  47:  5512 
    Google Scholar
  • 5e Crudden CM. Sateesh M. Lewis R. J. Am. Chem. Soc.  2005,  127:  10045 
    Google Scholar
  • 5f Kang C. Huang J. He W. Zhang F. J. Organomet. Chem.  2010,  695:  120 
    Google Scholar
  • 5g Mayr M. Mayr B. Buchmeiser MR. Angew. Chem. Int. Ed.  2001,  40:  3839 
    Google Scholar
  • 5h Byun JW. Lee YS. Tetrahedron Lett.  2004,  45:  1837 
    Google Scholar
  • 5i Kim JH. Jun BH. Byun JW. Lee YS. Tetrahedron Lett.  2004,  45:  5827 
    Google Scholar
  • 6a Kim JW. Kim JH. Lee D. Lee Y. Tetrahedron Lett.  2006,  47:  4745 
    Google Scholar
  • 6b Uozumi Y. Top. Curr. Chem.  2004,  242:  77 
    Google Scholar
  • 6c Guino M. Hii KKM. Chem. Soc. Rev.  2007,  36:  608 
    Google Scholar
  • 7a Wang S. Zhang Z. Hu Z. Wang Y. Lei P. Chi H. J. Environ. Sci.  2009,  21:  S124 
    Google Scholar
  • 7b Pelagatti P. Carcelli M. Costa M. Ianelli S. Pelizzi C. Rogolino D. J. Mol. Catal. A: Chem.  2005,  226:  107 
    Google Scholar
  • 7c Kang YK. Kim DY. Tetrahedron Lett.  2006,  27:  4565 
    Google Scholar
  • 8a Cai M. Sha J. Xu Q. J. Mol. Catal. A: Chem.  2007,  268:  82 
    Google Scholar
  • 8b Wolf C. Lerebours R. Org. Biomol. Chem.  2004,  2:  2161 
    Google Scholar
  • 8c Zhao H. Wang Y. Sha J. Sheng S. Cai M. Tetrahedron  2008,  64:  7517 
    Google Scholar
  • 8d Uozumi Y. Danjo H. Hayashi T. Tetrahedron Lett.  1998,  39:  8303 
    Google Scholar
  • 8e Uozumi Y. Danjo H. Hayashi T. J. Org. Chem.  1999,  64:  3384 
    Google Scholar
  • 8f Uozumi Y. Nakai Y. Org. Lett.  2002,  4:  2997 
    Google Scholar
  • 8g Uozumi Y. Kikuchi M. Synlett  2005,  1775 
    Google Scholar
  • 9a Phan NTS. Styring P. Green Chem.  2008,  10:  1055 
    Google Scholar
  • 9b Mohanty S. Suresh D. Balakrishna MS. Mague JT. J. Organomet. Chem.  2009,  694:  2114 
    Google Scholar
  • 10 King RB. Sweet EM. J. Org. Chem.  1979,  44:  385 
    CrossrefGoogle Scholar
  • 11 Kharasch MS. Seyler RC. Mayo FR. J. Am. Chem. Soc.  1983,  60:  822 
    Google Scholar
  • 12 Onue H. Moritani I. J. Organomet. Chem.  1972,  43:  431 
    CrossrefGoogle Scholar
  • 13 Durig JR. Layton R. Sink DW. Mitchell BR. Spectrochim. Acta  1965,  21:  1367 
    CrossrefGoogle Scholar
  • 14 Santra PK. Sagar P. J. Mol. Catal. A: Chem.  2003,  197:  37 
    CrossrefGoogle Scholar
  • 15a Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
    Google Scholar
  • 15b Suzuki A. J. Organomet. Chem.  1999,  576:  147 
    Google Scholar
  • 15c Suzuki A. J. Organomet. Chem.  2002,  653:  83 
    Google Scholar
  • 15d Miyaura N. Top. Curr. Chem.  2002,  11 
    Google Scholar
  • 15e Miyaura N. Metal-Catalyzed Cross-Coupling Reactions   2nd ed., Vol. 1:  de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004.  p.41-124  
    Google Scholar
  • 16a Sonogashira K. J. Organomet. Chem.  2002,  653:  46 
    Google Scholar
  • 16b Negishi E. Anastasia L. Chem. Rev.  2003,  103:  1979 
    Google Scholar
  • 17a Sin E. Yi S. Lee Y. J. Mol. Catal. A: Chem.  2010,  315:  99 
    Google Scholar
  • 17b Wang L. Cai C. J. Mol. Catal. A: Chem.  2009,  306:  97 
    Google Scholar
  • 17c Bandini M. Luque R. Budarin V. Macquarrie DJ. Tetrahedron  2005,  61:  9860 
    Google Scholar
  • 17d Bakherad M. Keivanloo A. Bahramian B. Hashemi M. Tetrahedron Lett.  2009,  50:  1557 
    Google Scholar
  • 17e Liang B. Dai M. Chen J. Yang Z. J. Org. Chem.  2005,  70:  391 
    Google Scholar