Advertisement

Catalysis Letters

, Volume 147, Issue 1, pp 188–195 | Cite as

Silica-Supported Ni(II)–DABCO Complex: An Efficient and Reusable Catalyst for the Heck Reaction

  • Abdol R. Hajipour
  • Parisa Abolfathi
Article

Abstract

An interesting nickel-based catalyst supported on DABCO-functionalized silica was successfully prepared and evaluated as heterogeneous nanocatalyst in Heck cross coupling reaction of various aryl halides and methyl acrylate. The as-prepared nanocatalyst was well characterized by FT-IR, FE-SEM, TEM, XRD, SEM-EDX, ICP and TGA techniques and found to be highly efficient in the reaction system in terms of activity and recyclability.

Graphical Abstract

This work provides an economical and heterogeneous catalytic system based nickel nanoparticle supported on DABCO functionalized silica for the Heck cross-coupling reaction of various aryl halides with methyl acrylate.

Keywords

DABCO Nickel(II) Heterogenous catalyst Mizoroki–Heck reaction 

Notes

Acknowledgments

We gratefully acknowledge the funding support received for this project from the Isfahan University of Technology (IUT), IR of Iran, and Isfahan Science and Technology Town (ISTT), IR of Iran. Further financial support from the Center of Excellence in Sensor and Green Chemistry Research (IUT) is gratefully acknowledged.

Supplementary material

10562_2016_1880_MOESM1_ESM.docx (61 kb)
Supplementary material 1 (DOCX 60 KB)

References

  1. 1.
    Diederich F, Stang PJ (2008) John Wiley & Sons, New YorkGoogle Scholar
  2. 2.
    Tsuji J (2002) John Wiley & Sons, New YorkGoogle Scholar
  3. 3.
    Jana R, Pathak TP, Sigman MS (2011) Chem Rev 111:1417–1492CrossRefGoogle Scholar
  4. 4.
    Wang L, Li P, Zhang Y (2004) Chem Commun 5:514–515CrossRefGoogle Scholar
  5. 5.
    Yang CT, Zhang ZQ, Liu YC, Liu L (2011) Angew Chem Int Ed 123:3990–3993CrossRefGoogle Scholar
  6. 6.
    Zhang L, Zuo Z, Leng X, Huang Z (2014) Angew Chem Int Ed 53:2696CrossRefGoogle Scholar
  7. 7.
    Adeli M, Mehdipour E, Bavadi M (2010) J Appl Polym Sci 116:2188–2196Google Scholar
  8. 8.
    Magano J, Dunetz J (2011) Chem Rev 11:2177–2250CrossRefGoogle Scholar
  9. 9.
    Nicolaou KC, Bulger PG, Sarlah D (2005) Angew Chem Int Ed 44:4442–4489CrossRefGoogle Scholar
  10. 10.
    Bobes FG, Fu GC (2006) J Am Chem Soc 128:5360–5361CrossRefGoogle Scholar
  11. 11.
    Leowanawat P, Zhang N, Resmerita AM, Rosen BM, Percec V (2011) J Org Chem 76:9946–9995CrossRefGoogle Scholar
  12. 12.
    Knappke CEI, von Wangelin AJ (2010) Angew Chem Int Ed 49:3568–3570CrossRefGoogle Scholar
  13. 13.
    Hu X (2011) Chem Sci 2:1867–1886CrossRefGoogle Scholar
  14. 14.
    Zultanski SL, Fu GC (2013) J Am Chem Soc 135:624–627CrossRefGoogle Scholar
  15. 15.
    Zhang N, Hoffman DJ, Gutsche N, Gupta J, Percec V (2012) J Org Chem 77:5956–5964CrossRefGoogle Scholar
  16. 16.
    Xian YL, Guo WH, He GZ, Pan Q, Zhang X (2014) Angew Chem Int Ed 53:1CrossRefGoogle Scholar
  17. 17.
    Matsubara R, Gutierrez AC, Jamison TF (2011) J Am Chem Soc 133:19020–19023CrossRefGoogle Scholar
  18. 18.
    Tasker SZ, Gutierrez AC, Jamison TF (2014) Angew Chem Int Ed 53:1858–1861CrossRefGoogle Scholar
  19. 19.
    Liu C, Tang S, Liu D, Yuan J, Zheng L, Meng L, Lei A (2012) Angew Chem Int Ed 51:3638–3641CrossRefGoogle Scholar
  20. 20.
    Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita AM, Garg NK, Percec V (2010) Chem Rev 111:1346–1416CrossRefGoogle Scholar
  21. 21.
    Han FS (2013) Chem Soc Rev 42:5270–5298CrossRefGoogle Scholar
  22. 22.
    Zhao YL, Li Y, Li SM, Zhou YG, Sun FY, Gao LX, Han FS (2011) Adv Synth Catal 353:1543–1550CrossRefGoogle Scholar
  23. 23.
    Li XJ, Zhang JL, Geng Y, Jin Z (2013) J Org Chem 78:5078–5084CrossRefGoogle Scholar
  24. 24.
    Kuroda JI, Inamoto K, Hiroya K (2009) Eur J Org Chem 14:2251–2261CrossRefGoogle Scholar
  25. 25.
    Sharma RK, Pandey A, Gulati S (2012) Polyhedron 45:86–93CrossRefGoogle Scholar
  26. 26.
    Sharma RK, Pandey A, Gulati S (2012) Appl Catal A 431:33–41CrossRefGoogle Scholar
  27. 27.
    Sharma RK, Gulati S (2012) J Mol Catal A Chem 363:291–303CrossRefGoogle Scholar
  28. 28.
    Sharma RK, Rawat D (2012) Inorg Chem Commun 17:58–63CrossRefGoogle Scholar
  29. 29.
    Sharma RK, Sharma C (2011) Catal Commun 12:327–331CrossRefGoogle Scholar
  30. 30.
    Sharma RK, Sharma C (2010) J Mol Catal A Gen 332:53–58CrossRefGoogle Scholar
  31. 31.
    Sharma RK, Sharma S (2014) Dalton Trans 43:1292–1304CrossRefGoogle Scholar
  32. 32.
    Sharma RK, Sharma S, Gaba G (2014) RSC Adv 4:49198–49211CrossRefGoogle Scholar
  33. 33.
    Isfahani AL, Mohammadpoor-Baltork I, Mirkhani V, Khosropour AR, Moghadam M, Tangestaninejad S, Kia R (2013) Adv Synth Catal 355:957–972CrossRefGoogle Scholar
  34. 34.
    Singh B, Jain SL, Rana BS, Khatri PK, Sinha AK, Sain B (2010) ChemCatChem 2:1260–1264CrossRefGoogle Scholar
  35. 35.
    Hajipour AR, Boostani E, Mohammadsaleh F (2015) RSC Adv 5:24742–24748CrossRefGoogle Scholar
  36. 36.
    Kim JH, Kim JW, Shokouhimehr M, Lee YS (2005) J Org Chem 70:6714–6720CrossRefGoogle Scholar
  37. 37.
    Nimkar A, Ramana M, Betkar R, Ranade P, Mundhe B (2016) New J Chem 40:2541–2546CrossRefGoogle Scholar
  38. 38.
    Kannisto H, Arve K, Pingel T, Hellman A, Harelind H, Eranen K, Olsson E, Skoglundh M, Murzin DY (2013) Catal Sci Tech 3:644–653CrossRefGoogle Scholar
  39. 39.
    Kandepi VKM, Narender N (2012) Catal Sci Tech 2:471–487CrossRefGoogle Scholar
  40. 40.
    Magne V, Garnier T, Danel M, Pale P, Chassaing S (2015) Org Lett 17:4494–4497CrossRefGoogle Scholar
  41. 41.
    Pan HB, Wai CM (2011) New J Chem 35:1649–1660CrossRefGoogle Scholar
  42. 42.
    Cornelio B, Rance GA, Laronze-Cochard M, Fontana A, Sapi J, Khlobystov AN (2013) J Mater Chem A 1:8737–8744CrossRefGoogle Scholar
  43. 43.
    Rodriguez-Perez L, Pradel C, Serp P, Gomez M, Teuma E (2011) ChemCatChem 3:749–754CrossRefGoogle Scholar
  44. 44.
    Sairanen E, Karinen R, Borghei M, Kauppinen EI, Lehtonen J (2012) ChemCatChem 4:2055–2061CrossRefGoogle Scholar
  45. 45.
    Amadio E, Scrivanti A, Chessa G, Matteoli U, Beghetto V, Bertoldini M, Rancan M, Dolmella A, Venzo A, Bertani R (2012) J Organomet Chem 716:193–200CrossRefGoogle Scholar
  46. 46.
    Ranganath KV, Onitsuka S, Kumar AK, Inanaga J (2013) Catal Sci Tech 3:2161–2181CrossRefGoogle Scholar
  47. 47.
    Xu Y, Zhang Z, Zheng J, Du Q, Li Y (2013) Appl Organomet Chem 27:13–18CrossRefGoogle Scholar
  48. 48.
    Ornelas C, Ruiz J, Salmon L, Astruc D (2008) Adv Synth Catal 350:837–845CrossRefGoogle Scholar
  49. 49.
    Hajipour AR, Azizi G (2013) Green Chem 15: 1030–1034CrossRefGoogle Scholar
  50. 50.
    Hajipour AR, Azizi G (2014) RSC Adv 4:20704–20708CrossRefGoogle Scholar
  51. 51.
    Hajipour AR, Azizi G (2014) Chin J Catal 35: 1547–1554CrossRefGoogle Scholar
  52. 52.
    Hajipour AR, Hosini DM, Mohammadsaleh F (2016) New J Chem. doi: 10.1039/c6nj00612d
  53. 53.
    Beheshtia YS, Khorshidi M, Heravi MM, Baghernejad B (2010) Eur J Chem 3:232–235CrossRefGoogle Scholar
  54. 54.
    Hasaninejad A, Shekouhy M, Golzar N, Zare A, Doroodmand MM (2011) Appl Catal A Gen 402:11–22CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  1. 1.Pharmaceutical Research Laboratory, Department of ChemistryIsfahan University of TechnologyIsfahanIran
  2. 2.Department of Neuroscience, Medical SchoolUniversity of WisconsinMadisonUSA

Personalised recommendations