Skip to main content
Log in

Tetrazole Functionalized Polymer Supported Palladium Complex: An Efficient and Reusable Catalyst for the Room-Temperature Suzuki Cross-Coupling Reaction

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Tetrazole functionalized polymer supported palladium complex was synthesized and characterized. The catalytic activity has been evaluated for the room-temperature Suzuki cross-coupling reaction proving an excellent performance in terms of both activity and recyclability. Various aryl bromides were coupled with aryl boronic acids in EtOH/H2O mixed solvents, under air and in presence of 0.5 mol% of the catalyst to afford corresponding cross-coupled products in high yields. Furthermore, the heterogeneous catalyst can be readily recovered by simple filtration and reused for several times only with slightly decrease in its activity.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Scheme 3

Similar content being viewed by others

References

  1. Miyaura N, Yamada K, Suzuki A (1979) Tetrahedron Lett 20:3437

    Article  Google Scholar 

  2. Miyaura N, Suzuki A (1995) Chem Rev 95:2457

    Article  CAS  Google Scholar 

  3. Diederich J (1998) Metal-catalyzed cross-coupling reaction. Wiley-Interscience, New York

    Book  Google Scholar 

  4. Negishi E, de Meijere A (2002) Handbook of organopalladium chemistry for organic synthesis. Wiley-Interscience, New York

    Google Scholar 

  5. Littke AF, Fu GC (1998) Angew Chem Int Ed 37:3387

    Article  CAS  Google Scholar 

  6. Zapf A, Ehrentraut A, Beller M (2000) Angew Chem Int Ed 39:4153

    CAS  Google Scholar 

  7. Walker SD, Barder TE, Martinelli JR, Buchwald SL (2004) Angew Chem Int Ed 43:1871

    Article  CAS  Google Scholar 

  8. Wolf C, Ekoue-Kovi K (2006) Eur J Org Chem 2006:1917

    Article  Google Scholar 

  9. O’Brien CJ, Kantchev EAB, Valente C, Hadei N, Chass GA, Lough A, Hopkinson AC, Organ MG (2006) Chem Eur J 12:4743

    Article  Google Scholar 

  10. Brendgen T, Frank M, Schatz J (2006) Eur J Org Chem 2006:2378

    Article  Google Scholar 

  11. Dai WM, Zhang Y (2005) Tetrahedron Lett 46:1377

    Article  CAS  Google Scholar 

  12. Kovala-Demertzi D, Kourkoumelis N, Derlat K, Michalak J, Andreadaki FJ, Kostas ID (2008) Inorg Chim Acta 361:1562

    Article  CAS  Google Scholar 

  13. Chen W, Li R, Han B, Li BJ, Chen YC, Wu Y, Ding LS, Yang D (2006) Eur J Org Chem 2006:1177

    Article  Google Scholar 

  14. Phan NTS, Van Der Sluys M, Jones CW (2006) Adv Synth Catal 348:609

    Article  CAS  Google Scholar 

  15. De Vos DE, Dams M, Sels BF, Jacobs PA (2002) Chem Rev 102:3615

    Article  Google Scholar 

  16. Yin L, Liebsher J (2007) Chem Rev 107:133

    Article  CAS  Google Scholar 

  17. Maegawa T, Kitamura Y, Sako S, Udzu T, Sakurai A, Tanaka A, Kobayashi Y, Endo K, Bora U, Kurita T, Kozaki A, Monguchi Y, Sajiki H (2007) Chem Eur J 13:5937

    Article  CAS  Google Scholar 

  18. Lee D, Kim J, Jun B, Kang H, Park J, Lee Y (2008) Org Lett 10:1609

    Article  CAS  Google Scholar 

  19. Zhang J, Zhang W, Wang Y, Zhang M (2008) Adv Synth Catal 350:2065

    Article  CAS  Google Scholar 

  20. Trzeciak AM, Mieczynska E, Ziolkowsky J, Bukowski W, Bukowska A, Noworol J, Okal J (2008) New J Chem 32:1124

    Article  CAS  Google Scholar 

  21. Yamada YMA, Takeda K, Takahashi H, Ikegami S (2002) Org Lett 4:3371

    Article  CAS  Google Scholar 

  22. Yamada YMA, Takeda K, Takahashi H, Ikegami S (2003) J Org Chem 68:7733

    Article  CAS  Google Scholar 

  23. Ikegami S, Hamamoto H (2009) Chem Rev 109:583

    Article  CAS  Google Scholar 

  24. Mehnert CP, Weaver DW, Ying JY (1998) J Am Chem Soc 120:12289

    Article  CAS  Google Scholar 

  25. Dams M, Drijkoningen L, Pauwels B, Van Tendeloo G, De Vos DE, Jacobs PA (2002) J Catal 209:225

    Article  CAS  Google Scholar 

  26. Lin KH, Song MP, Cai DM, Hao XQ, Wu YJ (2003) Tetrahedron Lett 44:3955

    Article  CAS  Google Scholar 

  27. Varma RS, Naicker KP, Liesen PJ (1999) Tetrahedron Lett 40:2075

    Article  CAS  Google Scholar 

  28. Polshettiwar V, Varma RS (2008) Tetrahedron 64:4637

    Article  CAS  Google Scholar 

  29. McNamara CA, Dixon MJ, Bradley M (2002) Chem Rev 102:3275

    Article  CAS  Google Scholar 

  30. Beletskaya IP, Khokhlov AR, Tarasenko EA, Tyurin VS (2007) J Organomet Chem 692:4402

    Article  CAS  Google Scholar 

  31. Polshettiwar V, Molnár Á (2007) Tetrahedron 63:6949

    Article  CAS  Google Scholar 

  32. Zhou H, Zhuo GL, Jiang XZ (2006) J Mol Catal A Chem 248:26

    Article  CAS  Google Scholar 

  33. Andrushko V, Schwinn D, Tzschucke CC, Michalek F, Horn J, Mossner C, Bannwarth W (2005) Helv Chim Acta 88:936

    Article  CAS  Google Scholar 

  34. Gonzalez-Arellano C, Corma A, Iglesias M, Sanchez F (2004) Adv Synth Catal 346:1316

    Article  CAS  Google Scholar 

  35. Chang Y, Lv YR, Lu F, Zha F, Lei ZG (2010) J Mol Catal A Chem 320:56

    Article  CAS  Google Scholar 

  36. Li Y, Fu X, Gong B, Zou X, Tu X, Chen J (2010) J Mol Catal A Chem 322:55

    Article  CAS  Google Scholar 

  37. Byun JW, Lee YS (2004) Tetrahedron Lett 45:1837

    Article  CAS  Google Scholar 

  38. Steel PG, Teasdale CWT (2004) Tetrahedron Lett 45:8977

    Article  CAS  Google Scholar 

  39. Kim JH, Kim JW, Shokouhimehr M, Lee YS (2005) J Org Chem 70:6714

    Article  CAS  Google Scholar 

  40. Kim JW, Kim JH, Lee DH, Lee YS (2006) Tetrahedron Lett 47:4745

    Article  CAS  Google Scholar 

  41. Garcia-Martinez JC, Scott RWJ, Crooks RM (2003) J Am Chem Soc 125:11190

    Article  CAS  Google Scholar 

  42. van Heerbeek R, Kamer PCJ, van Leeuwen P, Reek JNH (2002) Chem Rev 102:3717

    Article  Google Scholar 

  43. Inada K, Miyaura N (2000) Tetrahedron 56:8661

    Article  CAS  Google Scholar 

  44. Parrish CA, Buchwald SL (2001) J Org Chem 66:3820

    Article  CAS  Google Scholar 

  45. Glegola K, Framery E, Pietrusiewicz KM, Sinou D (2006) Adv Synth Catal 348:1728

    Article  CAS  Google Scholar 

  46. Sommer WJ, Weck M (2006) Adv Synth Catal 348:2101

    Article  CAS  Google Scholar 

  47. Bedford RB, Coles SJ, Hursthouse MB, Scordia VJM (2005) Dalton Trans 2005:991

    Article  Google Scholar 

  48. Leyva A, García H, Corma A (2007) Tetrahedron 63:7097

    Article  CAS  Google Scholar 

  49. Colacot TJ, Carole WA, Neide BA, Harad A (2008) Organometallics 27:5605

    Article  CAS  Google Scholar 

  50. Schweizer S, Becht JM, Drian CL (2010) Tetrahedron 66:765

    Article  CAS  Google Scholar 

  51. Ornelas C, Diallo AK, Ruiz J, Astruc D (2009) Adv Synth Catal 351:2147

    Article  CAS  Google Scholar 

  52. Gupta AK, Song CH, Oh CH (2004) Tetrahedron Lett 45:4113

    Article  CAS  Google Scholar 

  53. Meyer E, Joussef AC, Gallardo H (2003) Synthesis 6:899

    Google Scholar 

  54. Cassol CC, Umpierre AP, Machado G, Wolke SI, Dupont J (2005) J Am Chem Soc 127:3298

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Chun Cai.

Rights and permissions

Reprints and permissions

About this article

Cite this article

He, Y., Cai, C. Tetrazole Functionalized Polymer Supported Palladium Complex: An Efficient and Reusable Catalyst for the Room-Temperature Suzuki Cross-Coupling Reaction. Catal Lett 140, 153–159 (2010). https://doi.org/10.1007/s10562-010-0415-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-010-0415-z

Keywords

Navigation