Skip to main content
SpringerLink
Log in

Bioinspired Palladium Nanoparticles Supported on Soil-Derived Humic Acid Coated Iron-Oxide Nanoparticles as Catalyst for C–C Cross-Coupling and Reduction Reactions

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Pd nanoparticles supported on humic acid-coated nanoferrites as magnetically-recoverable catalyst was expediently prepared from inexpensive precursors and characterized by techniques such as SEM, TEM, XPS, FT-IR, XRD, ICP-AES, EDX. The as made catalyst displayed an admirable catalytic activity towards the Suzuki–Miyaura cross-coupling reaction of aryl halides (or) aryl diazonium salts with aryl boronic acid in non-toxic solvent EtOH/water under mild conditions. The same catalyst showed high efficiency for the Heck reaction of aryl halides with styrene was carried out with high efficiency offering good yields under ligand-free conditions. Additionally, the reduction of olefins using molecular hydrogen was also achieved using the same catalyst under ambient and base-free conditions affording the products in good to excellent yields. The magnetic activity of nano-Fe3O4 allowed the effortless recovery of the catalyst and demonstrated subsequent recyclability up to 5 cycles without a significant loss in the 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
Fig. 8

Similar content being viewed by others

References

  1. Molnár (2011) Á Chem Rev 111:2251

    Article  CAS  PubMed  Google Scholar 

  2. Hartwig JF Nature (2008) 455: 314

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Blaser HU, Catal Today (2000) 60:161

    Article  CAS  Google Scholar 

  4. Busacca CA, Fandrick DR, Song JJ, Senanayake CH (2011) Adv Synt Catal 353:1825

    Article  CAS  Google Scholar 

  5. Vandenberg EJ (1992) Catalysis in polymer synthesis. American Chemical Society, Washington, DC, pp 2–23

    Book  Google Scholar 

  6. Feng J, Holmes M, Krische MJ (2017) Chem Rev 117:12564

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Trost BM (1995) Angew Chem Int Ed 34:259

    Article  CAS  Google Scholar 

  8. Fumagalli G, Stanton S, Bower J (2017) F, Chem Rev 117:9404

    Article  CAS  PubMed  Google Scholar 

  9. Chen X, Engle KM, Wang DH, Yu JQ (2009) Ang Chem Int Ed 48:5094

    Article  CAS  Google Scholar 

  10. Polshettiwar V, Luque R, Fihri A, Zhu H, Bouhrara M, Basset J-M (2011) Chem Rev 111:3036

    Article  CAS  PubMed  Google Scholar 

  11. Wang D, Astruc D (2017) Chem Soc Rev 46:816

    Article  CAS  PubMed  Google Scholar 

  12. Zhang S, Nguyen L, Zhu Y, Zhan S, Tsung CK, Tao F (2013) Acc Chem Res 46:1731

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  14. Veisi H, Nasrabadi NH, Mohammadi P (2016) Appl Organomet Chem 30:890

    Article  CAS  Google Scholar 

  15. Lebaschi S, Hekmati M, Veisi HJ (2017) Colloid Interface Sci 485:223

    Article  CAS  Google Scholar 

  16. Veisi H, Faraji AR, Hemmati S, Gil A (2015) Appl Organomet Chem 29:517

    Article  CAS  Google Scholar 

  17. Das SK, Parandhaman T, Pentela N et al (2014) J Phys Chem C 118:24623

    Article  CAS  Google Scholar 

  18. Veisi H, Pirhayati M, Kakanejadifard A et al ChemistrySelect (2018) 3:1820

    Article  CAS  Google Scholar 

  19. Karimi B, Mansouri F, Mirzaei HM, ChemCatChem (2015) 7:1736

  20. Dubey AV, Kumar AV, Adv RSC (2016) 6:46864

    Article  CAS  Google Scholar 

  21. Farzad E, Veisi H (2018) J Ind Eng Chem 60:114

    Article  CAS  Google Scholar 

  22. Baig RBN, Varma RS (2012) Chem Commun 48:2582

    Article  CAS  Google Scholar 

  23. Nasir Baig RB, Leazer J, Varma RS, Clean Technol Environ Policy (2015), 17:2073

  24. Dam B, Patil RA, Ma YR, Pal AK (2017) New J Chem 41:6553

    Article  CAS  Google Scholar 

  25. Jha A, Patil CR, Garade AC, Rode CV (2013) Ind Eng Chem Res 52:9803

    Article  CAS  Google Scholar 

  26. Yi DK, Lee SS, Ying JY (2006) Chem Mater 18:2459

    Article  CAS  Google Scholar 

  27. Sharma RK, Yadav M, Gawande MB (2016) In: Eds.: Sharma VK, Doong R, Kim H, Varma RS, Dionysiou DD ACS Symp Ser. American Chemical Society, Washington, DC, pp 1–38

  28. Heidari F, Hekmati M, Veisi H (2017) J Colloid Interface Sci 501:175

    Article  CAS  PubMed  Google Scholar 

  29. Rehm TH, Bogdan A, Hofmann C, Löb P, Shifrina ZB, Morgan DG, Bronstein LM (2015) ACS Appl Mater Interfaces 7:27254

    Article  CAS  PubMed  Google Scholar 

  30. Deraedt C, Wang D, Salmon L, Etienne L, Labrugère C, Ruiz J, Astruc D, ChemCatChem (2015) 7:303

    Article  CAS  Google Scholar 

  31. Asadi B, Mohammadpoor-Baltork I, Tangestaninejad S, Moghadam M, Mirkhani V, Landarani-Isfahani A (2016) New J Chem 40:6171

    Article  CAS  Google Scholar 

  32. Paez JI, Froimowicz P, Landfester K, Brunetti V, Strumia M (2014) J Polym Sci Part A 52:3185

    Article  CAS  Google Scholar 

  33. Safaei S, Mohammadpoor-Baltork I, Khosropour AR, Moghadam M, Tangestaninejad S, Mirkhani V, Kia R (2012) RSC Adv 2:5610

    Article  CAS  Google Scholar 

  34. Zheng X, Luo S, Zhang L, Cheng JP (2009) Green Chem 11:455

    Article  CAS  Google Scholar 

  35. Otokesh S, Kolvari E, Amoozadeh A, Koukabi N, RSC Adv (2015) 5:53749

  36. Zhang Q, Su H, Luo J, Wei Y (2012) Green Chem 14:201

    Article  CAS  Google Scholar 

  37. Mandal P, Chattopadhyay AP, Dalton Trans (2015), 44:11444

    Article  CAS  PubMed  Google Scholar 

  38. Jamatia R, Gupta A, Pal AK (2017) ACS Sustain Chem Eng 5:7604

    Article  CAS  Google Scholar 

  39. Veisi H, Pirhayati M, Kakanejadifard A (2017) Tetrahedron Lett 58:4269

    Article  CAS  Google Scholar 

  40. Zhang M, Liu YH, Shang ZR, Hu HC, Zhang ZH, Catal Commun (2017) 88:39

  41. Patil MR, Kapdi AR, Vijay Kumar A (2018) ACS Sustain Chem Eng 6:3264

    Article  CAS  Google Scholar 

  42. Ko S, Jang J (2006) Angew Chem Int Ed 45:7564

    Article  CAS  Google Scholar 

  43. Jawale DV, Gravel E, Boudet C et al (2015) Catal Sci Technol 5:2388

    Article  CAS  Google Scholar 

  44. Reddy LH, Arias JL, Nicolas J, Couvreur P (2012) Chem Rev 112:5818

    Article  CAS  PubMed  Google Scholar 

  45. Korneva G, Ye H, Gogotsi Y, Halverson D, Friedman G, Bradley JC, Kornev KG (2005) Nano Lett 5:879

    Article  CAS  PubMed  Google Scholar 

  46. Veisi H, Mirzaee N (2018) Appl Organomet Chem 32:e4067

    Article  CAS  Google Scholar 

  47. Yang S, Zong P, Ren X, Wang Q, Wang X (2012) ACS Appl Mater Interfaces 4:6891

    Article  CAS  PubMed  Google Scholar 

  48. Veisi H, Mohammadi Biabri P, Falahi H (2017) Tetrahedron Lett 58:3482

    Article  CAS  Google Scholar 

  49. Wang D, Liu W, Bian F, Yu W (2015) New J Chem 39:2052

  50. Parandhaman T, Pentela N, Ramalingam B et al (2017) ACS Sustain Chem Eng 5:489

    Article  CAS  Google Scholar 

  51. Veisi H, Najafi S, Hemmati S (2018) Int J Biol Macromol 113:186

    Article  CAS  PubMed  Google Scholar 

  52. Veisi H, Mirshokraie SA, Ahmadian H (2018) Int J Biol Macromol 108:419

    Article  CAS  PubMed  Google Scholar 

  53. Kharisov BI, Kharissova OV, Dias HVR (2014) Nanomaterials for environmental protection. Wiley, Hoboken, pp 483–501

    Google Scholar 

  54. Hu JD, Zevi Y, Kou XM, Xiao J, Wang XJ, Jin Y (2010) Sci Total Environ 408:3477

    Article  CAS  PubMed  Google Scholar 

  55. Ni L, Su L, Li S, Wang P, Li D, Ye X, Li Y, Li Y, Li Y, Wang C (2017) Environ Toxicol Chem 36:1856

    Article  CAS  PubMed  Google Scholar 

  56. Lippold H, Gottschalch U, Kupsch H (2008) Chemosphere 70:1979

    Article  CAS  PubMed  Google Scholar 

  57. Liu S, Zhu Y, Liu L, He Z, Giesy JP, Bai Y, Sun F, Wu F (2018) Environ Pollut 234:726

    Article  CAS  PubMed  Google Scholar 

  58. Tan L, Wang X, Tan X, Mei H, Chen C, Hayat T, Alsaedi A, Wen T, Lu S, Wang X (2017) Chem Geol 464:91

    Article  CAS  Google Scholar 

  59. Tang Z, Zhao X, Zhao T, Wang H, Wang P, Wu F, Giesy JP (2016) Environ Sci Technol 50:8640

    Article  CAS  PubMed  Google Scholar 

  60. Liu J, Zhao Z, Jiang G (2008) Environ Sci Technol 42:6949

    Article  CAS  PubMed  Google Scholar 

  61. Stevenson FJ, Goh KM (1971) Geochim Cosmochim Acta 35:471

    Article  CAS  Google Scholar 

  62. García-Suárez EJ, Balu AM, Tristany M, García AB, Philippot K, Luque R (2012) Green Chem 14:1434

    Article  CAS  Google Scholar 

  63. García CS, Uberman PM, Martín SE, Beilstein (2017) J Org Chem 13:1717

    Google Scholar 

  64. Sobhani S, Zarifi F, Chinese J, Catal (2015), 36:555

Download references

Acknowledgements

AVD is grateful to University Grants Commision (UGC) for the research fellowship. AVK is grateful to DST, Govt. of India, for research funding, DST-SERB (YSS/2015/002064) and the Department of Pharmaceutical Science and Technology, ICT, for NMR analysis. We are also thankful to Sophisticated Analytical Instruments Facility (SAIF) at the Indian Institute of Technology, Mumbai (IITB) for providing the characterization data for the analysis of the catalyst.

Author information

Author notes

  1. Anurag N. Chinchole and Abhishek V. Dubey have contributed equally.

Authors and Affiliations

  1. Department of Chemistry, Institute of Chemical Technology, Nathalal Parekh Marg, Matunga, Mumbai, Maharashtra, 400019, India

    Anurag N. Chinchole, Abhishek V. Dubey & A. Vijay Kumar

Authors
  1. Anurag N. Chinchole
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Abhishek V. Dubey
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Vijay Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. Vijay Kumar.

Additional information

Publisher’s Note

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

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1385 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chinchole, A.N., Dubey, A.V. & Kumar, A.V. Bioinspired Palladium Nanoparticles Supported on Soil-Derived Humic Acid Coated Iron-Oxide Nanoparticles as Catalyst for C–C Cross-Coupling and Reduction Reactions. Catal Lett 149, 1224–1236 (2019). https://doi.org/10.1007/s10562-019-02703-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-019-02703-z

Keywords

Search

Navigation