Skip to main content
SpringerLink
Log in

Ferrocene-tagged N-heterocyclic carbene-Pd complex for Suzuki–Miyaura coupling

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

We demonstrate that the ferrocene-tagged N-heterocyclic carbene (NHC)-Pd(II) complex can act as an efficient heterogeneous catalyst for Suzuki–Miyaura cross-coupling in dimethylformamide (DMF)-water. This complex was found to be an active and efficient catalyst for coupling of aryl iodides, bromides, and even less reactive chlorides with boronic acids and pinacol ester of boronic acid.

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

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Herrmann WA (2002) Angew Chem Int Ed 41:1290

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  3. Herrmann WA, Bohm VPW, Gstöttmayr CWK, Grosche M, Reisinger CP, Weskamp T (2001) J Organomet Chem 617:616

    Article  Google Scholar 

  4. Navarro O, Kelly RA, Nolan SP (2003) J Am Chem Soc 125:16194

    Article  CAS  Google Scholar 

  5. Navarro O, Kaur H, Mahjoor P, Nolan SP (2004) J Org Chem 69:3173

    Article  CAS  Google Scholar 

  6. Altenhoff G, Goddard R, Lehmann CW, Glorius F (2004) J Am Chem Soc 126:15195

    Article  CAS  Google Scholar 

  7. Enders D, Niemeier O, Henseler A (2007) Chem Rev 107:5606

    Article  CAS  Google Scholar 

  8. Hahn FE, Jahnke MC (2008) Angew Chem Int Ed 47:3122

    Article  CAS  Google Scholar 

  9. Metallinos C, Barrett FB, Chaytor JL, Heska MEA (2004) Org Lett 6:3641

    Article  CAS  Google Scholar 

  10. Siemeling U (2012) Eur J Inorg Chem 2012:3523

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

    Article  CAS  Google Scholar 

  12. Wang AE, Xie JH, Wang LX, Zhou QL (2005) Tetrahedron 61:259

    Article  CAS  Google Scholar 

  13. Benhamou L, Chardon E, Lavigne G, Bellemin-Laponnaz S, Cesar V (2011) Chem Rev 111:2705

    Article  CAS  Google Scholar 

  14. Kantchev EAB, O’Brien CJ, Organ MG (2007) Angew Chem Int Ed 46:2768

    Article  CAS  Google Scholar 

  15. Herrmann WA, Ofele K, Elison M, Kühn FE, Roesky PW (1994) J Organomet Chem 480:c7

    Article  CAS  Google Scholar 

  16. Ofele K, Herrmann WA, Mihalios D, Elison M, Herdtweck E, Scherer W, Mink J (1993) J Organomet Chem 459:177

    Article  Google Scholar 

  17. Garrou PE (1985) Chem Rev 85:171

    Article  CAS  Google Scholar 

  18. Chalkand AJ, Magennis SA (1976) J Org Chem 41:1206

    Article  Google Scholar 

  19. Cabri W, Candiani I, DeBernardinis S, Francalanci F, Penco S, Santo R (1991) J Org Chem 56:5796

    Article  CAS  Google Scholar 

  20. Togni A, Hayashi T (1995) Ferrocenes: homogeneous catalysis—organic synthesis—materials science. VCH, Weinheim

    Google Scholar 

  21. Togni A, Halterman RL (1998) Metallocenes. Wiley-VCH, Weinheim

    Book  Google Scholar 

  22. Long NJ (1998) Metallocenes: an introduction to sandwich complexes. Blackwell Science, Oxford

    Google Scholar 

  23. Atkinson RCJ, Gibson VC, Long NJ (2004) Chem Soc Rev 33:313

    Article  CAS  Google Scholar 

  24. Bildstein B (2001) J Organomet Chem 617:28

    Article  Google Scholar 

  25. Bildstein B, Malaun M, Kopacka H, Ongania KH, Wurst K (1998) J Organomet Chem 552:45

    Article  CAS  Google Scholar 

  26. Ren G, Cui X, Yang E, Yang F, Wu Y (2010) Tetrahedron 66:4022

    Article  CAS  Google Scholar 

  27. Ren G, Cui X, Wu Y (2010) Eur J Org Chem 12:2372

    Article  Google Scholar 

  28. Leng Y, Yang F, Wei K, Wu Y (2010) Tetrahedron 66:1244

    Article  CAS  Google Scholar 

  29. Zhao XM, Hao XQ, Wang KL, Liu JR, Song MP, Wu YJ (2009) Trans Metal Chem 34:683

    Article  CAS  Google Scholar 

  30. Mu B, Li T, Fu Z, Wu Y (2009) Catal Commun 10:1497

    Article  CAS  Google Scholar 

  31. Coleman KS, Turberville S, Pascu SI, Green MLH (2005) J Organomet Chem 690:653

    Article  CAS  Google Scholar 

  32. Willms H, Frank W, Ganter C (2008) Chem Eur J 14:2719

    Article  CAS  Google Scholar 

  33. Gaikwad DS, Park YK, Pore DM (2012) Tetrahedron Lett 53:3077

    Article  CAS  Google Scholar 

  34. Gaikwad DS, Pore DM (2012) Synlett 23:2631

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  36. Negishi EI (2011) Angew Chem Int Ed 50:738

    Article  Google Scholar 

  37. Liu C, Ni Q, Bao F, Qiu J (2011) Green Chem 13:260

    Google Scholar 

  38. Sau SC, Santra S, Sen TK, Mandal SK, Koley D (2012) Chem Commun 48:555

    Article  CAS  Google Scholar 

  39. Terashima T, Inomata S, Ogata K, Fukuzawa S (2012) Eur J Inorg Chem 2012:1387

  40. Nandurkar NS, Bhanage BM (2008) Tetrahedron 64:3655

    Article  CAS  Google Scholar 

  41. Qiu J, Wang L, Liu M, Shen Q, Tang J (2011) Tetrahedron Lett 48:6489

    Article  Google Scholar 

  42. Bai L, Wang J-X (2008) Adv Synth Catal 350:315

    Article  CAS  Google Scholar 

  43. Desmarets C, Amrani RO, Walcarius A, Lambert J, Champagne B, Fort Y, Schneider R (2008) Tetrahedron 64:372

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Author D.S.G. thanks UGC-SAP BSR New Delhi for a research fellowship.

Author information

Authors and Affiliations

  1. Department of Chemistry, Shivaji University, Kolhapur, 416 004, India

    Dattaprasad M. Pore, Dipak S. Gaikwad & Jayavant D. Patil

Authors
  1. Dattaprasad M. Pore
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Dipak S. Gaikwad
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jayavant D. Patil
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Dattaprasad M. Pore.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 4710 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pore, D.M., Gaikwad, D.S. & Patil, J.D. Ferrocene-tagged N-heterocyclic carbene-Pd complex for Suzuki–Miyaura coupling. Monatsh Chem 144, 1355–1361 (2013). https://doi.org/10.1007/s00706-013-0970-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-013-0970-2

Keywords

Search

Navigation