Skip to main content
SpringerLink
Log in

Recyclable and Reusable Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O System for Cyanation of Aryl Chlorides with Potassium Ferrocyanide

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Pd(OAc)2/XPhos–SO3Na in a mixture of poly(ethylene glycol) (PEG-400) and water is shown to be a highly efficient catalyst for the cyanation of aryl chlorides with potassium ferrocyanide. The reaction proceeded smoothly at 100 or 120 ºC with K2CO3 or KOAc as base, delivering a variety of aromatic nitriles in good to excellent yields. The isolation of the crude products is facilely performed by extraction with cyclohexane and more importantly, both expensive Pd(OAc)2 and XPhos–SO3Na in PEG-400/H2O system could be easily recycled and reused at least six times without any apparent loss of catalytic efficiency.

Graphical Abstract

Palladium-catalyzed cyanation of aryl chlorides with potassium ferrocyanide leading to aryl nitriles by using Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O as a highly efficient and recyclable catalytic system is described.

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
Scheme 2

Similar content being viewed by others

References

  1. Larock RC (1989) Comprehensive organic transformations. VCH, New York, pp 819–995

    Google Scholar 

  2. Fleming FF (1999) Nat Prod Rep 16:597–606

    Article  CAS  Google Scholar 

  3. Jones LH, Summerhill NW, Swain NA, Mills JE (2010) MedChemComm 1:309–318

    Article  CAS  Google Scholar 

  4. Rappoport Z (1970) Chemistry of the Cyano Group. Wiley, London, U.K.

    Google Scholar 

  5. Larock RC (1999) Comprehensive organic transformations: a guide to functional group preparations, 2nd edn. VCH, New York

    Google Scholar 

  6. Shim YJ, Lee HJ, Park J (2012) J Organomet Chem 696:4173–4178

    Article  CAS  Google Scholar 

  7. Okano T, Iwahara M, Kiji J (1998) Synletter 1998:243–244

    Article  Google Scholar 

  8. Littke A, Soumeillant M, Kaltenbach RF, Cherney RJ, Tarby CM, Kiau S (2007) Org Lett 9:1711–1714

    Article  CAS  PubMed  Google Scholar 

  9. Zhang XJ, Xia AY, Chen HY, Liu Y (2017) Org Lett 19:2118–2121

    Article  CAS  PubMed  Google Scholar 

  10. Jia X, Yang D, Zhang S, Cheng J (2009) Org Lett 11:4716–4719

    Article  CAS  PubMed  Google Scholar 

  11. Sundermeier M, Mutyala S, Zapf A, Spannenberg A, Beller M (2003) J Organomet Chem 684:50–55

    Article  CAS  Google Scholar 

  12. Schareina T, Zapf A, Cotte A, Gotta M, Beller M (2011) Adv Synth Catal 353:777–780

    Article  CAS  Google Scholar 

  13. Nasrollahzadeh M (2016) Tetrahedron Lett 57:337–339

    Article  CAS  Google Scholar 

  14. Schareina T, Zapf A, Beller M (2004) Chem Commun 2004:1388–1389

    Article  Google Scholar 

  15. Anbarasan P, Schareina T, Beller M (2011) Chem Soc Rev 40:5049–5067

    Article  CAS  PubMed  Google Scholar 

  16. Veisi H (2019) Polyhedron 159:212–216

    Article  CAS  Google Scholar 

  17. Veisi H, Tamoradi T, Karmakar B, Mohammadi P, Hemmati S (2019) Mater Sci Eng C 104:109919

    Article  CAS  Google Scholar 

  18. Baran T (2020) Carbohyd Polym 237:116105

    Article  CAS  Google Scholar 

  19. Caliskan M, Baran T (2021) Int J Biol Macromol 174:120–133

    Article  CAS  PubMed  Google Scholar 

  20. Baran T, Nasrollahzadeh M (2021) J Phys Chem Solids 149:109772

    Article  CAS  Google Scholar 

  21. Caliskan M, Baran T, Nasrollahzadeh M (2021) J Phys Chem Solids 152:109968

    Article  CAS  Google Scholar 

  22. Littke AF, Fu GC (2002) Angew Chem Int Ed 41:4176–4211

    Article  CAS  Google Scholar 

  23. Jin F, Confalone PN (2000) Tetrahedron Lett 41:3271–3273

    Article  CAS  Google Scholar 

  24. Schareina T, Zapf A, Magerlein W, Muller N, Beller M (2007) Tetrahedron Lett 50:1087–1090

    Article  CAS  Google Scholar 

  25. Schareina T, Jackstell R, Schulz T, Zapf A, Cotte A, Gotta M, Beller M (2009) Adv Synth Catal 351:643–648

    Article  CAS  Google Scholar 

  26. Sundermeier M, Zapf A, Mutyala S, Baumann W, Sans J, Weiss S, Beller M (2003) Chem Eur J 9:1828–1836

    Article  CAS  PubMed  Google Scholar 

  27. Sundermeier M, Zapf A, Beller M (2003) Angew Chem Int Ed 42:1661–1664

    Article  CAS  Google Scholar 

  28. Cohen DT, Buchwald SL (2015) Org Lett 17:202–205

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. Senecal TD, Shu W, Buchwald SL (2013) Angew Chem Int Ed 52:10035–10039

    Article  CAS  Google Scholar 

  30. Zhang J, Chen X, Hu T, Zhang Y, Xu K, Yu Y, Huang J (2010) Catal Lett 139:56–60

    Article  CAS  Google Scholar 

  31. Yeung PY, So CM, Lau CP, Kwong FY (2011) Org Lett 13:648–651

    Article  CAS  PubMed  Google Scholar 

  32. Anastas PT, Warner JC (1998) Green Chemistry: Theory and Practice. Oxford University Press, UK

    Google Scholar 

  33. Clarke CJ, Tu W-C, Levers O, Bröhl A, Hallett JP (2018) Chem Rev 118:747–800

    Article  CAS  PubMed  Google Scholar 

  34. Ohki T, Harada M, Okada T (2007) J Phys Chem B 111:7245–7252

    Article  CAS  PubMed  Google Scholar 

  35. Chandrasekhar S, Narsihmulu C, Sultana SS, Reddy NR (2002) Org Lett 4:4399–4401

    Article  CAS  PubMed  Google Scholar 

  36. Declerck V, Colacino E, Bantreil X, Martinez J, Lamaty F (2012) Chem Commun 48:11778–11780

    Article  CAS  Google Scholar 

  37. Li JH, Liu WJ, Xie YX (2005) J Org Chem 70:5409–5412

    Article  CAS  PubMed  Google Scholar 

  38. Liu L, Zhang Y, Wang Y (2005) J Org Chem 70:6122–6125

    Article  CAS  PubMed  Google Scholar 

  39. Wang L, Zhang Y, Liu L, Wang Y (2006) J Org Chem 71:1284–1287

    Article  CAS  PubMed  Google Scholar 

  40. Ackermann L, Vicente R (2009) Org Lett 11:4922–4925

    Article  CAS  PubMed  Google Scholar 

  41. Zhou Q, Wei S, Han W (2014) J Org Chem 79:1454–1460

    Article  CAS  PubMed  Google Scholar 

  42. Chandrasekhar S, Prakash SJ, Rao CL (2006) J Org Chem 71:2196–2199

    Article  CAS  PubMed  Google Scholar 

  43. Chandrasekhar S, Sultana SS, Yaragorla SR, Reddy NR (2006) Synthesis 2006:839–842

    Article  CAS  Google Scholar 

  44. Bantreil X, Sidi-Ykhlef M, Aringhieri L, Colacino E, Martinez J, Lamaty F (2012) J Catal 294:113–118

    Article  CAS  Google Scholar 

  45. Zhao H, Zhang T, Yan T, Cai M (2015) J Org Chem 80:8849–8855

    Article  CAS  PubMed  Google Scholar 

  46. Yedage SL, Bhanage BM (2016) Green Chem 18:5635–5642

    Article  CAS  Google Scholar 

  47. Billault I, Pessl F, Petit A, Turgis R, Scherrmann M-C (2015) New J Chem 39:1986–1995

    Article  CAS  Google Scholar 

  48. Patil NM, Bhanage BM (2016) ChemCatChem 8:3458–3462

    Article  CAS  Google Scholar 

  49. Xu C, Huang B, Yan T, Cai M (2018) Green Chem 20:391–397

    Article  CAS  Google Scholar 

  50. Patil NM, Sasaki T, Bhanage BM (2016) ACS Sustainable Chem Eng 4:429–436

    Article  CAS  Google Scholar 

  51. Anderson KW, Buchwald SL (2005) Angew Chem Int Ed 44:6173–6177

    Article  CAS  Google Scholar 

  52. Reetz M, Lohmer G (1996) Chem Commun 1996:1921–1922

    Article  Google Scholar 

Download references

Acknowledgements

We thank the National Natural Science Foundation of China (No. 21462021) and the Natural Science Foundation of Jiangxi Province of China (No. 20161BAB203086) for financial support.

Author information

Authors and Affiliations

  1. College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang, 330022, People’s Republic of China

    Mingzhong Cai, Mingzhong Cai, Rong Liu, Caifeng Xu & Bin Huang

Authors
  1. Mingzhong Cai
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rong Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Caifeng Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Bin Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Mingzhong Cai or Bin Huang.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Cai, M., Liu, R., Xu, C. et al. Recyclable and Reusable Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O System for Cyanation of Aryl Chlorides with Potassium Ferrocyanide. Catal Lett 152, 2688–2694 (2022). https://doi.org/10.1007/s10562-021-03864-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-021-03864-6

Keywords

Search

Navigation