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Synthesis 2011(2): 243-250  
DOI: 10.1055/s-0030-1258349
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Simple, Efficient, and Recyclable Phosphine-Free Catalytic System for Carbonylative Suzuki Coupling Reaction of Aryl and Heteroaryl Iodides

Ziyauddin S. Qureshi, Krishna M. Deshmukh, Pawan J. Tambade, Bhalchandra M. Bhanage*
Department of Chemistry, Institute of Chemical Technology (Autonomous), N. Parekh Marg, Matunga, Mumbai 400 019, India
Fax: +91(22)24145614; e-Mail: bhalchandra_bhanage@yahoo.com; e-Mail: bm.bhanage@ictmumbai.edu.in;
Further Information

Publication History

Received 11 October 2010
Publication Date:
03 December 2010 (online)

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Abstract

The carbonylative Suzuki cross-coupling reaction of arylboronic acid with aryl and heteroaryl iodides using polymer supported palladium-N-heterocyclic carbene complex (PS-Pd-NHC) as an efficient heterogeneous, recyclable catalyst is described. The developed catalytic system is found to be effective for the carbonylative coupling reaction of aryl, heteroaryl, and bicyclic heteroaryl iodides (5-iodoindole and 3-iodoquinoline) with various arylboronic acid derivatives providing good to excellent yields of the desired products. The protocol is advantageous due to the ease in handling of the catalyst and simple workup procedure, and environmentally benign with effective catalyst recyclability.

Key words

biaryl ketones - boron - heterogeneous catalysis - palladium - Suzuki carbonylation

    References

  • 1 The Merck Index   11th ed.:  Budavari S. Merck; Rahway: 1989. 
    Google Scholar
  • 2a Fürstner A. Voigtländer D. Schrader W. Giebel D. Reetz MT. Org. Lett.  2001,  3:  417 
    Google Scholar
  • 2b Song CE. Shim WH. Roh EJ. Choi JH. Chem. Commun.  2000,  1695 
    Google Scholar
  • 2c Fillion E. Fishlock D. Wilsily A. Goll JM. J. Org. Chem.  2005,  70:  1316 
    Google Scholar
  • 3a Bonnaire S. Carpentier JF. Mortreux A. Castanet Y. Tetrahedron Lett.  2001,  42:  3689 
    Google Scholar
  • 3b Bonnaire S. Carpentier JF. Mortreux A. Castanet Y. Tetrahedron  2003,  59:  2793 
    Google Scholar
  • 4 Ishiyama T. Kizaki H. Hayashi T. Suzuki A. Miyaura N. J. Org. Chem.  1998,  63:  4726 
    CrossrefGoogle Scholar
  • 5 Maerten E. Hassouna F. Bonnaire S. Mortreux A. Carpentier JF. Castanet Y. Synlett  2003,  1874 
    Article in Thieme ConnectGoogle Scholar
  • 6 Andrus MB. Ma Y. Zang Y. Song C. Tetrahedron Lett.  2002,  43:  9137 
    Google Scholar
  • 7 Cai M. Zheng G. Zha L. Peng J. Eur. J. Org. Chem.  2009,  1585 
    Google Scholar
  • 8 Mingji D. Liang B. Wang C. You Z. Xiang J. Dong G. Chen J. Yang Z. Adv. Synth. Catal.  2004,  346:  1669 
    CrossrefGoogle Scholar
  • 9 Neumann H. Brennfhrer A. Beller M. Adv. Synth. Catal.  2008,  350:  2437 
    CrossrefGoogle Scholar
  • 10 Petz A. Peczely G. Pinter Z. Kollar L. J. Mol. Catal. A: Chem.  2006,  255:  97 
    CrossrefGoogle Scholar
  • 11a Ofele K. J. Organomet. Chem.  1968,  12:  42 
    Google Scholar
  • 11b Wanzlick HJ. Schönherr HJ. Angew. Chem. Int. Ed.  1968,  7:  141 
    Google Scholar
  • 11c Herrmann WA. Angew. Chem. Int. Ed.  2002,  41:  1290 
    Google Scholar
  • 12a Weskamp T. Kohl FJ. Hieringer W. Gleich D. Herrmann WA. Angew. Chem. Int. Ed.  1999,  38:  2416 
    Google Scholar
  • 12b Schwarz J. Biihm VPW. Gardiner MG. Grosche M. Herrmann WA. Hieringer W. Raudaschl-Sieber G. Chem. Eur. J.  2000,  6:  1773 
    Google Scholar
  • 13a Byun JW. Lee YS. Tetrahedron Lett.  2004,  45:  1837 
    Google Scholar
  • 13b Kim JW. Kim JH. Lee DH. Lee YS. Tetrahedron Lett.  2006,  47:  4745 
    Google Scholar
  • 13c Tandukar S. Sen A. J. Mol. Catal., A: Chem.  2007,  268:  112 
    Google Scholar
  • 13d Gomann A. Deverell JA. Munting KF. Jones RC. Rodemann T. Canty AJ. Smith JA. Guijt RM. Tetrahedron  2009,  65:  1450 
    Google Scholar
  • 14a Tambade PJ. Patil YP. Bhanage BM. Appl. Organomet. Chem.  2009,  23:  235 
    Google Scholar
  • 14b Tambade PJ. Patil YP. Bhanushali MJ. Bhanage BM. Synthesis  2008,  2347 
    Google Scholar
  • 14c Tambade PJ. Patil YP. Bhanushali MJ. Bhanage BM. Tetrahedron Lett.  2008,  49:  2221 
    Google Scholar
  • 14d Tambade PJ. Patil YP. Panda AG. Bhanage BM. Eur. J. Org. Chem.  2009,  3022 
    Google Scholar
  • 15a Lempers HEB. Sheldon RA. J. Catal.  1998,  175:  62 
    Google Scholar
  • 15b Zhao H. Zheng G. Sheng S. Cai M. Catal. Commun.  2009,  11:  158 
    Google Scholar