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;
Weitere Informationen

Publikationsverlauf

Received 11 October 2010
Publikationsdatum:
03. Dezember 2010 (eFirst)

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.

    References

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