Skip to main content
SpringerLink
Log in

Suzuki–Miyaura Cross-Coupling in Aqueous Medium Using Recyclable Palladium/Amide-Silica Catalyst

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Silica-immobilized benzamide palladium complex was prepared and characterized. The complex exhibits excellent catalytic activity and stability for Suzuki–Miyaura cross-coupling reaction under mild aqueous reaction condition. Various aryl bromides were coupled with arylboronic acids in i-PrOH/H2O, under open air at room temperature, in the presence of 0.22 mol% of the catalyst to afford corresponding cross-coupled products in high yields. Furthermore, the novel heterogeneous catalyst can be conveniently recovered by simple filtration and reused several times without significant loss in activity.

Graphical Abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

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

    Article  CAS  Google Scholar 

  2. Suzuki A (2011) Angew Chem Int Ed 50:6722

    Article  CAS  Google Scholar 

  3. Fihri A, Bouhrara M, Nekoueishahraki B, Basset JM, Polshettiwar V (2011) Chem Soc Rev 40:5181

    Article  CAS  Google Scholar 

  4. Sellars JD, Steel PG (2011) Chem Soc Rev 40:5170

    Article  CAS  Google Scholar 

  5. Maluenda I, Navarro O (2015) Molecules 20:7528

    Article  CAS  Google Scholar 

  6. Liu C, Li X (2016) Chem Rec 16:84

    Article  CAS  Google Scholar 

  7. Das P, Linert W (2016) Coord Chem Rev 311:1

    Article  CAS  Google Scholar 

  8. Nicolaou KC, Bulger PG, Sarlah D (2005) Angew Chem Int Ed 44:4442

    Article  CAS  Google Scholar 

  9. Kotha S, Lahiri K, Kashinath D (2002) Tetrahedron 58:9633

    Article  CAS  Google Scholar 

  10. Magano J, Dunetz JR (2011) Chem Rev 111:2177

    Article  CAS  Google Scholar 

  11. Torborg C, Beller M (2009) Adv Synth Catal 351:3027

    Article  CAS  Google Scholar 

  12. Naso F, Babudri F, Farinola GM (1999) Pure Appl Chem 71:1485

    Article  CAS  Google Scholar 

  13. Fleckenstein CA, Plenio H (2010) Chem Soc Rev 39:694

    Article  CAS  Google Scholar 

  14. Bellina F, Carpita A, Rossi R (2004) Synthesis 15:2419

    Google Scholar 

  15. Kostas ID, Tenchiu AC, Arbez-Dindre C, Psycharis V, Rapropoulou CP (2014) Catal Commun 51:15

    Article  CAS  Google Scholar 

  16. Herrmann WA, Reisinger CP, Spiegler MJ (1998) J Organomet Chem 557:93

    Article  CAS  Google Scholar 

  17. Marion N, Nolan SP (2008) Acc Chem Res 41:1440

    Article  CAS  Google Scholar 

  18. Fortman GC, Nolan SP (2011) Chem Soc Rev 40:5151

    Article  CAS  Google Scholar 

  19. Schaper LA, Hock SJ, Herrmann WA, Kühn FE (2013) Angew Chem Int Ed 52:270

    Article  CAS  Google Scholar 

  20. Grasa GA, Viciu MS, Huang J, Zhang C, Trudell ML, Nolan SP (2002) Organometallics 21:2866

    Article  CAS  Google Scholar 

  21. Zhang J, Zhao L, Song M, Mak TCW, Wu Y (2006) J Organomet Chem 691:1301

    Article  CAS  Google Scholar 

  22. Alonso DA, Najera C (2010) Chem Soc Rev 39:2891

    Article  CAS  Google Scholar 

  23. Lee S (2006) J Organomet Chem 691:1347

    Article  CAS  Google Scholar 

  24. Amadio E, Scrivanti A, Beghetto V, Bertoldini M, Alam MM, Matteoli U (2013) RSC Adv 3:21636

    Article  CAS  Google Scholar 

  25. Ye C, Chen Z, Wang H, Wu J (2012) Tetrahedron 68:5197

    Article  CAS  Google Scholar 

  26. Tao B, Boykin DW (2004) J Org Chem 69:4330

    Article  CAS  Google Scholar 

  27. Li JH, Liu WJ (2004) Org Lett 6:2809

    Article  CAS  Google Scholar 

  28. Banik B, Tairai A, Shahnaz N, Das P (2012) Tetrahedron Lett 53:5627

    Article  CAS  Google Scholar 

  29. Dewan A, Bora U, Borah G (2014) Tetrahedron Lett 55:1689

    Article  CAS  Google Scholar 

  30. Rao GK, Kumar A, Kumar B, Kumar D, Singh AK (2012) Dalton Trans 41:1931

    Article  CAS  Google Scholar 

  31. Mondal M, Bora U (2014) Tetrahedron Lett 55:3038

    Article  CAS  Google Scholar 

  32. Arumugam V, Kaminsky W, Bhuvanesh NSP, Nallasamy D (2015) RSC Adv 5:59428

    Article  CAS  Google Scholar 

  33. Leadbeater NE (2005) Chem Commun 23:2881

    Article  Google Scholar 

  34. Saha D, Chattopadhyay K, Ranu BC (2009) Tetrahedron Lett 50:1003

    Article  CAS  Google Scholar 

  35. Mondal M, Bora U (2012) Green Chem 14:1873

    Article  CAS  Google Scholar 

  36. Decorrignies A, Fihri A, Azemar G, Djedaini-Pilard F, Len C (2013) Catal Commun 32:101

    Article  Google Scholar 

  37. Xiang L, Xiaohua Z, Ming L (2013) Appl Organometal Chem 27:615

    CAS  Google Scholar 

  38. Liu C, Rao X, Song X, Qiu J, Jin Z (2013) RSC Adv 2:526

    Article  Google Scholar 

  39. Liu L, Dong Y, Pang B, Ma J (2014) J Org Chem 79:7193

    Article  CAS  Google Scholar 

  40. Sarmah G, Mondal M, Bora U (2015) Appl Organometal Chem 29:495

    Article  CAS  Google Scholar 

  41. Paul S, Islam MM, Islam SM (2015) RSC Adv 5:42193

    Article  CAS  Google Scholar 

  42. Crudden CM, Sateesh M, Lewis R (2005) J Am Chem Soc 127:10045

    Article  CAS  Google Scholar 

  43. Yin L, Liebscher J (2007) Chem Rev 107:133

    Article  CAS  Google Scholar 

  44. Faria VW, Oliveira DGM, Kurz MHS, Gonçalves FF, Scheeren CW, Rosa GR (2014) RSC Adv 4:13446

    Article  CAS  Google Scholar 

  45. Karami K, Ghasemi M, Naeini NH (2013) Catal Commun 38:10

    Article  CAS  Google Scholar 

  46. Nandi M, Uyama H (2014) RSC Adv 4:20847

    Article  CAS  Google Scholar 

  47. Le X, Dong Z, Jin Z, Wang Q, Ma J (2014) Catal Commun 53:47

    Article  CAS  Google Scholar 

  48. Singh AK, Rao GK, Kumar A, Singh MP, Saleem F, Kumar S (2015) RSC Adv 5:20081

    Article  Google Scholar 

  49. Patel KN, Bedekar AV (2015) Catal Lett 145:1710

    Article  CAS  Google Scholar 

  50. Veerakumar P, Velayudham M, Lu KL, Rajagopal S (2013) Appl Catal A 455:247

    Article  CAS  Google Scholar 

  51. Martínez A, Krinsky JL, Peñafiel I, Castillón S, Loponov K, Lapkin A, Godard C, Claver C (2015) Catal Sci Technol 5:310

    Article  Google Scholar 

  52. Polshettiwar V, Len C, Fihri A (2009) Coord Chem Rev 253:2599

    Article  CAS  Google Scholar 

  53. Sarmah C, Sahu D, Das P (2012) Catal Today 198:197

    Article  CAS  Google Scholar 

  54. Begum T, Mondal M, Gogoi PK, Bora U (2015) RSC Adv 2015(5):38085

    Article  Google Scholar 

  55. Dhara K, Sarkar K, Srimani D, Saha SK, Chattopadhyay P, Bhaumik A (2010) Dalton Trans 39:6395

    Article  CAS  Google Scholar 

  56. Demel J, Sujandi, Park SE, Cejka J, Stepnicka P (2009) J Mol Catal: A Chem 302:28

    Article  CAS  Google Scholar 

  57. Sing KSW, Everett DH, Haul RAW, Moscou L, Pierotti RA, Rouquerol J, Siemieniewska T (1985) Pure Appl Chem 57:603

    Article  CAS  Google Scholar 

  58. Pavia C, Giacalone F, Bivona LA, Salvo AMP, Petrucci C, Strappaveccia G, Vaccaro L, Aprile C, Gruttadauria M (2014) J Mol Cat A: Chem 387:57

    Article  CAS  Google Scholar 

  59. Richardson JM, Jones CW (2007) J Catal 251:80

    Article  CAS  Google Scholar 

  60. Widegren JA, Finke RG (2003) J Mol Cat A: Chem 198:317

    Article  CAS  Google Scholar 

  61. Liu F, Feng G, Lin M, Wang C, Hu B, Qi C (2014) J Colloid Interface Sci 435:83

    Article  CAS  Google Scholar 

  62. Whitesides GM, Hackett M, Brainard RL, Lavalleye JPPM, Sowinski AF, Izumi AN, Moore SS, Brown DW, Staudt EM (1985) Organometallics 4:819

    Article  Google Scholar 

  63. Paal C, Hartmann W (1918) Chem Ber 51:711

    Article  CAS  Google Scholar 

  64. Anton DR, Crabtree RH (1983) Organometallics 2:855

    Article  CAS  Google Scholar 

  65. Lewis LN, Lewis N (1986) J Am Chem Soc 108:7228

    Article  CAS  Google Scholar 

  66. Lin Y, Finke RG (1994) Inorg Chem 33:4891

    Article  CAS  Google Scholar 

  67. Weddle KS, Aiken JD III, Finke RG (1998) J Am Chem Soc 120:5653

    Article  CAS  Google Scholar 

  68. van Asselt R, Elsevier CJ (1991) J Mol Catal 65:L13

    Article  Google Scholar 

  69. Foley P, DiCosimo R, Whitesides GM (1980) J Am Chem Soc 102:6713

    Article  CAS  Google Scholar 

  70. Süss-Fink G, Faure M, Ward TR (2002) Angew Chem Int Ed 41:99

    Article  Google Scholar 

  71. Lewis LN (1986) J Am Chem Soc 108:743

    Article  CAS  Google Scholar 

  72. Hajipour AR, Shirdashtzade Z, Azizi G (2014) J Chem Sci 126:85

    Article  CAS  Google Scholar 

  73. Tong X, Zhao Y, Huang T, Liu H, Liew KY (2009) Appl Surf Sci 255:9463

    Article  CAS  Google Scholar 

  74. Kitamura Y, Sako S, Tsutsui A, Monguchi Y, Maegawa T, Kitade Y, Sajiki H (2010) Adv Synth Catal 352:718

    Article  CAS  Google Scholar 

  75. Zhou WJ, Wang KH, Wang JX, Gao Z-R (2010) Tetrahedron 66:7633

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Dr. A. Dewan acknowledges UGC-New Delhi for Dr. D. S. Kothari Postdoctoral fellowship. Dr. M. Mondal and T. Begum are thankful to UGC, New Delhi for financial assistance in the form of UGC-BSR (RFSMS) Fellowship. SAIF (STIC), Cochin is acknowledged for ICP-AES analytical service.

Author information

Authors and Affiliations

  1. Department of Chemistry, Dibrugarh University, Dibrugarh, Assam, 786004, India

    Manoj Mondal, Tahshina Begum & Pradip K. Gogoi

  2. Department of Chemical Sciences, Tezpur University, Tezpur, Assam, 784028, India

    Anindita Dewan, Ashim Jyoti Thakur & Utpal Bora

Authors
  1. Manoj Mondal
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anindita Dewan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tahshina Begum
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Pradip K. Gogoi
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ashim Jyoti Thakur
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Utpal Bora
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Manoj Mondal or Utpal Bora.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mondal, M., Dewan, A., Begum, T. et al. Suzuki–Miyaura Cross-Coupling in Aqueous Medium Using Recyclable Palladium/Amide-Silica Catalyst. Catal Lett 146, 1718–1728 (2016). https://doi.org/10.1007/s10562-016-1796-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-016-1796-4

Keywords

Search

Navigation