Skip to main content

Green Synthesis of Palladium Nanoparticles: Applications in Aryl Halide Cyanation and Hiyama Cross-Coupling Reaction Under Ligand Free Conditions

Catalysis Letters volume 148, pages 1562–1578 (2018)Cite this article

Abstract

In the current work, palladium nanoparticles (Pd NPs) were prepared from palladium acetate biogenically using the aqueous-ethanolic extract of black pepper (Piper nigrum) and characterized by various analytical techniques like XRD, FE-SEM, EDS, TEM, ATR-IR, UV–Vis spectroscopy, BET, TGA and ICP-OES analysis. The reduction of Pd(II) to Pd(0) is achieved by the action of various phytochemicals present in the black pepper extract like phenols, acids, pellitorine, ethyl piperonyl cyanoacetate, piperine and N-isobutyl-tetradeca-2,4-dienamide. The biosynthesized Pd NPs shown excellent catalytic activity in aryl halide cyanation and Hiyama cross-coupling reactions. Also, less toxic potassium hexacyanoferrate(II) trihydrate was used as cyanide source in aryl halide cyanation and Hiyama cross-coupling was performed under fluoride free condition. Both reactions proceeded well with Pd NPs under ligand free circumstances to give good to excellent yields. The Pd NPs were recovered after each reaction and recycled up to five times in aryl halide cyanation and ten times in Hiyama cross-coupling without considerable loss in the activity.

Graphical Abstract

Green synthesis of palladium nanoparticles: applications in aryl halide cyanation and Hiyama cross-coupling reaction under ligand free conditions.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

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

Fig. 1
Fig. 2
Scheme 1
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Fig. 15

References

  1. Kelly KL, Coronado E, Zhao LL, Schatz GC (2003) J Phys Chem B 107(3):668–677

    Article  CAS  Google Scholar 

  2. Burda C, Chen X, Narayanan R, El-Sayed MA (2005) Chem Rev 105(4):1025–1102

    Article  CAS  PubMed  Google Scholar 

  3. McConnell WP, Novak JP, Brousseau LC III, Fuierer RR, Tenent RC, Feldheim DL (2000) J Phys Chem B 104:8925–8930

    Article  CAS  Google Scholar 

  4. Dupont J, Fonseca GS, Umpierre AP, Fichtner PFP, Teixeira SR (2002) J Am Chem Soc 124(16):4228–4229

    Article  CAS  PubMed  Google Scholar 

  5. Narayanan R, El-Sayed MA (2005) J Phys Chem B 109(26):12663–12676

    Article  CAS  PubMed  Google Scholar 

  6. Ghosh S (2004) Appl Catal A 268(1–2):61–66

    Article  CAS  Google Scholar 

  7. Pong B-K, Elim HI, Chong J-X, Ji W, Trout BL, Lee J-Y (2007) J Phys Chem C 111(17):6281–6287

    Article  CAS  Google Scholar 

  8. Wu ZG, Munoz M, Montero O (2010) Adv Powder Technol 21(2):165–168

    Article  CAS  Google Scholar 

  9. Akhtar MS, Panwar J, Yun Y-S (2013) ACS Sustain Chem Eng 1(6):591–602

    Article  CAS  Google Scholar 

  10. Nasrollahzadeh M, Sajjadi M, Maham M, Sajadi SM, Barzinjy AA (2018) Mater Res Bull 102:24–35

    Article  CAS  Google Scholar 

  11. Maryami M, Nasrollahzadeh M, Mehdipour E, Sajadi SM (2017) Sep Purif Technol 184:298–307

    Article  CAS  Google Scholar 

  12. Nasrollahzadeh M, Issaabadi Z, Sajadi SM (2018) Sep Purif Technol 197:253–260

    Article  CAS  Google Scholar 

  13. Khazaei M, Khazaei A, Nasrollahzadeh M, Tahsili MR (2017) Tetrahedron 73(38):5613–5623

    Article  CAS  Google Scholar 

  14. Khodadadi B, Bordbar M, Nasrollahzadeh M (2017) J Colloid Interface Sci 490:1–10

    Article  CAS  PubMed  Google Scholar 

  15. Nasrollahzadeh M, Mohammad Sajadi S (2016) J Colloid Interface Sci 462:243–251

    Article  CAS  PubMed  Google Scholar 

  16. Atarod M, Nasrollahzadeh M, Sajadi SM (2016) J Colloid Interface Sci 465:249–258

    Article  CAS  PubMed  Google Scholar 

  17. Iravani S (2011) Green Chem 13(10):2638–2650

    Article  CAS  Google Scholar 

  18. Ahmed S, Ahmad M, Swami BL, Ikram S (2016) J Adv Res 7(1):17–28

    Article  CAS  PubMed  Google Scholar 

  19. Nisha P, Singhal RS, Pandit AB (2009) J Food Eng 92(1):44–49

    Article  CAS  Google Scholar 

  20. Ahmad N, Fazal H, Abbasi BH, Farooq S, Ali M, Khan MA (2012) Asian Pac J Trop Biomed 2(3):S1945-S1953

    Article  Google Scholar 

  21. Nahak G, Sahu RK (2011) J Appl Pharm Sci 08:153–157

    Google Scholar 

  22. Jirovetz L, Buchbauer G, Ngassoum MB, Geissler M (2002) J Chromatogr A 976(1–2):265–275

    Article  CAS  PubMed  Google Scholar 

  23. Yu H, Richey RN, Miller WD, Xu J, May SA (2011) J Org Chem 76(2):665–668

    Article  CAS  PubMed  Google Scholar 

  24. Chatterjee T, Dey R, Ranu BC (2014) J Org Chem 79(12):5875–5879

    Article  CAS  PubMed  Google Scholar 

  25. Nasrollahzadeh M (2016) Tetrahedron Lett 57(3):337–339

    Article  CAS  Google Scholar 

  26. Nasrollahzadeh M, Jaleh B, Fakhri P, Zahraei A, Ghadery E (2015) RSC Adv 5(4):2785–2793

    Article  CAS  Google Scholar 

  27. Nasrollahzadeh M, Momeni SS, Sajadi SM (2017) J Colloid Interface Sci 506:471–477

    Article  CAS  PubMed  Google Scholar 

  28. Sakamoto T, Ohsawa K (1999) J Chem Soc Perkin Trans 1(16):2323–2326

    Article  Google Scholar 

  29. Sundermeier M, Zapf A, Beller M, Sans J (2001) Tetrahedron Lett 42(38):6707–6710

    Article  CAS  Google Scholar 

  30. Ushkov AV, Grushin VV (2011) J Am Chem Soc 133(28):10999–11005

    Article  CAS  PubMed  Google Scholar 

  31. Sundermeier M, Mutyala S, Zapf A, Spannenberg A, Beller M (2003) J Organomet Chem 684(1–2):50–55

    Article  CAS  Google Scholar 

  32. Sato N (2002) Tetrahedron Lett 43(36):6403–6404

    Article  CAS  Google Scholar 

  33. Schareina T, Zapf A, Cotté A, Gotta M, Beller M (2011) Adv Synth Catal 353(5):777–780

    Article  CAS  Google Scholar 

  34. Kim J, Kim HJ, Chang S (2012) Angew Chem Int Ed 51(48):11948–11959

    Article  CAS  Google Scholar 

  35. Schareina T, Zapf A, Beller M (2004) Chem Commun 12:1388–1389

    Article  Google Scholar 

  36. Schareina T, Zapf A, Beller M (2004) J Organomet Chem 689(24):4576–4583

    Article  CAS  Google Scholar 

  37. Nasrollahzadeh M, Atarod M, Sajadi SM (2017) J Colloid Interface Sci 486:153–162

    Article  CAS  PubMed  Google Scholar 

  38. Nasrollahzadeh M, Sajadi SM (2016) J Colloid Interface Sci 469:191–195

    Article  CAS  PubMed  Google Scholar 

  39. Erhardt S, Grushin VV, Kilpatrick AH, Macgregor SA, Marshall WJ, Roe DC (2008) J Am Chem Soc 130(14):4828–4845

    Article  CAS  PubMed  Google Scholar 

  40. Yeung PY, So CM, Lau CP, Kwong FY (2011) Org Lett 13(4):648–651

    Article  CAS  PubMed  Google Scholar 

  41. Velmathi S, Leadbeater NE (2008) Tetrahedron Lett 49(32):4693–4694

    Article  CAS  Google Scholar 

  42. Senecal TD, Shu W, Buchwald SL (2013) Angew Chem Int Ed 52(38):10035–10039

    Article  CAS  Google Scholar 

  43. Chen G, Weng J, Zheng Z, Zhu X, Cai Y, Cai J, Wan Y (2008) Eur J Org Chem 20:3524–3528

    Article  CAS  Google Scholar 

  44. Nasrollahzadeh M, Issaabadi Z, Tohidi MM, Sajadi SM (2018) Chem Rec 18(2):165–229

    Article  CAS  PubMed  Google Scholar 

  45. Khazaei A, Khazaei M, Nasrollahzadeh M (2017) Tetrahedron 73(38):5624–5633

    Article  CAS  Google Scholar 

  46. Nasrollahzadeh M, Atarod M, Alizadeh M, Hatamifard A, Sajadi S (2017) Curr Org Chem 21(8):708–749

    Article  CAS  Google Scholar 

  47. Nasrollahzadeh M, Sajadi SM (2016) J Colloid Interface Sci 465:121–127

    Article  CAS  PubMed  Google Scholar 

  48. Nakao Y, Hiyama T (2011) Chem Soc Rev 40(10):4893–4901

    Article  CAS  PubMed  Google Scholar 

  49. Sore HF, Galloway WR, Spring DR (2012) Chem Soc Rev 41(5):1845–1866

    Article  CAS  PubMed  Google Scholar 

  50. Denmark SE, Regens CS (2008) Acc Chem Res 41(11):1486–1499

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  51. Denmark SE (2009) J Org Chem 74(8):2915–2927

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  52. Singh NK, Kumar P, Gupta DK, Singh S, Singh VK (2011) Pharm Lett 3:178–182

    CAS  Google Scholar 

  53. Mondal B, Acharyya K, Howlader P, Mukherjee PS (2016) J Am Chem Soc 138(5):1709–1716

    Article  CAS  PubMed  Google Scholar 

  54. Sajadi SM, Maham M, Mahmoud SA (2013) J Chem Res 37(10):620–622

    Article  CAS  Google Scholar 

  55. Suresh Kumar B, Amali AJ, Pitchumani K (2015) ACS Appl Mater Interfaces 7(41):22907–22917

    Article  CAS  PubMed  Google Scholar 

  56. Hajipour AR, Karami K, Tavakoli G, Pirisedigh A (2011) J Organomet Chem 696(4):819–824

    Article  CAS  Google Scholar 

  57. Magdesieva TV, Nikitin OM, Zolotukhina EV, Vorotyntsev MA (2014) Electrochim Acta 122:289–295

    Article  CAS  Google Scholar 

  58. Nasrollahzadeh M, Sajadi SM, Honarmand E, Maham M (2015) New J Chem 39(6):4745–4752

    Article  CAS  Google Scholar 

  59. Modak A, Mondal J, Bhaumik A (2012) Green Chem 14(10):2840–2855

    Article  CAS  Google Scholar 

  60. Srimani D, Sawoo S, Sarkar A (2007) Org Lett 9(18):3639–3642

    Article  CAS  PubMed  Google Scholar 

  61. Duran Pachon L, Thathagar MB, Hartl F, Rothenberg G (2006) Phys Chem Chem Phys 8(1):151–157

    Article  CAS  PubMed  Google Scholar 

  62. Shi S, Zhang Y (2007) J Org Chem 72(15):5927–5930

    Article  CAS  PubMed  Google Scholar 

  63. Sajiki H, Monguchi Y, Yanase T, Mori S (2012) Synthesis 45(01):40–44

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors thank Nano Mission, Ministry of Science & Technology, Department of Science & Technology, Government of India, for financial support through the Grant SR/NM/NS-20/2014. Authors also thank SAIF, CUSAT and SAIF, IITM for the analytical support.

Author information

Authors and Affiliations

  1. Centre for Nano and Material Sciences, Jain University, Jain Global Campus, Kanakapura, Ramanagaram, Bangalore, 562112, India

    Vishal Kandathil, Ramesh B. Dateer & Siddappa A. Patil

  2. Organic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum, 695019, India

    B. S. Sasidhar

  3. Pharmaceutical Sciences Department, College of Pharmacy, Rosalind Franklin University of Medicine and Science, North Chicago, IL, 60064, USA

    Shivaputra A. Patil

Authors
  1. Vishal Kandathil
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ramesh B. Dateer
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. S. Sasidhar
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Shivaputra A. Patil
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Siddappa A. Patil
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Siddappa A. Patil.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1568 KB)

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Kandathil, V., Dateer, R.B., Sasidhar, B.S. et al. Green Synthesis of Palladium Nanoparticles: Applications in Aryl Halide Cyanation and Hiyama Cross-Coupling Reaction Under Ligand Free Conditions. Catal Lett 148, 1562–1578 (2018). https://doi.org/10.1007/s10562-018-2369-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-018-2369-5

Keywords

  • Biogenic synthesis
  • Piper nigrum
  • Palladium nanoparticles
  • Cyanation reaction
  • Hiyama cross-coupling
  • Recycle