Skip to main content
SpringerLink
Log in

Novel Ionic Tagged Amine Anchored on Magnetic Nanoparticles: An Efficient and Magnetically Recyclable Catalyst for Phospha-Michael Addition

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Ionic tagged propyl amine immobilized on magnetic nanoparticles (MNPs) was synthesized and fully characterized. The novel catalyst (MNPs@PA-IL) was applied in phospha-Michael addition and gave the desired β-phosphonomalonates in good yields. The MNPs supported catalyst with ionic tag could be readily recovered from the reaction mixture using an external magnet. Compared with ionic-free counterpart (MNPs@PA), MNPs@PA-IL present better catalytic activity. The proposed mechanism regarding the MNPs@PA-IL catalyzed phospha-Michael reaction was also discussed.

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
Scheme 2
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. He HW, Wang T, Yuan JL (2005) J Organomet Chem 690:2608–2613

    Article  CAS  Google Scholar 

  2. Baylis EK, Campell CD, Dingwall JG (1984) J Chem Soc Perkin Trans 1:2845–2853

    Article  Google Scholar 

  3. Atheron FR, Hassal CH, Lambert RW (1986) J Med Chem 29:29–40

    Article  Google Scholar 

  4. Patel VD, Schmidt RJ, Biller SA, Gordon EM, Robinson SS, Manne V (1995) J Med Chem 38:2906–2921

    Article  CAS  Google Scholar 

  5. Silvestrini G, Zini N, Sabatelli P, Mocetti P, Maraldi NM, Bonucci E (1996) Bone 18:559–565

    Article  CAS  Google Scholar 

  6. Kafarski P, Lejczak B (1991) Phosphorous Sulfur Silicon Relat Elem 63:193–215

    Article  CAS  Google Scholar 

  7. Sobhani S, Tashrifi Z (2010) Tetrahedron 66:1429–1439

    Article  CAS  Google Scholar 

  8. Maryanoff BE, Reitz AB (1989) Chem Rev 89:863–927

    Article  CAS  Google Scholar 

  9. Doherty S, Elsegood MRJ, Clegg W, Ward MF, Waugh M (1997) Organometallics 16:4251–4253

    Article  CAS  Google Scholar 

  10. Gielen M, Dalil H, Ghys L, Boduszek B, Tiekink ERT, Matins JC, Biesemans M, Willem R (1998) Organometallics 17:4259–4262

    Article  CAS  Google Scholar 

  11. Doronina EP, Sidorkin VF, Lazareva NF (2010) Organometallics 29:3340

    Article  Google Scholar 

  12. Bunlaksananusorn T, Knochel P (2002) Tetrahedron Lett 43:5817–5819

    Article  CAS  Google Scholar 

  13. Hosseini-Sarvari M, Etemad S (2008) Tetrahedron 64:5519–5523

    Article  CAS  Google Scholar 

  14. Kulkarni MA, Pandurangi VR, Desai UV, Wadgaonkar PP (2012) C R Chim 15:745–752

    Article  CAS  Google Scholar 

  15. Jiang Z, Zhang Y, Ye W, Tan CH (2007) Tetrahedron Lett 48:51–54

    Article  CAS  Google Scholar 

  16. Hindersinn RR, Ludington RS (1965) J Org Chem 30:4020–4025

    Article  CAS  Google Scholar 

  17. Shulyupin MO, Kazankova MA, Beletskaya IP (2002) Org Lett 4:761–763

    Article  CAS  Google Scholar 

  18. Xu Q, Han LB (2006) Org Lett 8:2099–2101

    Article  CAS  Google Scholar 

  19. Greenberg S, Stephan DW (2008) Chem Soc Rev 37:1482–1489

    Article  CAS  Google Scholar 

  20. Semmenzin D, Etemad-Moghadam G, Albouy D, Diallo O, Koenig M (1997) J Org Chem 62:2414–2422

    Article  Google Scholar 

  21. Han LB, Zhao CQ (2005) J Org Chem 70:10121–10123

    Article  CAS  Google Scholar 

  22. Kolla SR, Lee YR (2012) Tetrahedron 68:228–237

    Article  Google Scholar 

  23. Stockland RA, Taylor RI, Thompson LE, Patel PB (2005) Org Lett 7:851–853

    Article  CAS  Google Scholar 

  24. Lenker HK, Richard ME, Reese KP, Carter AF, Zawisky JD, Winter EF, Bergeron TW, Guydon KS, Stockland RA (2012) J Org Chem 77:1378–1385

    Article  CAS  Google Scholar 

  25. Sobhani S, Rezazadeh S (2010) Synlett 10:1485–1488

    Article  Google Scholar 

  26. Sobhani S, Parizi ZP, Rezazadeh S (2011) J Organomet Chem 696:813–817

    Article  CAS  Google Scholar 

  27. Lu AH, Salabas EL, Schüth F (2007) Angew Chem Int Ed 46:1222–1244

    Article  CAS  Google Scholar 

  28. Gawande MB, Branco PS, Varma RS (2013) Chem Soc Rev 42:3371–3393

    Article  CAS  Google Scholar 

  29. Baig RBN, Varma RS (2013) Chem Commun 49:752–770

    Article  CAS  Google Scholar 

  30. Riente P, Yadav J, Pericàs MA (2012) Org Lett 14:3668–3671

    Article  CAS  Google Scholar 

  31. Roy S, Pericàs MA (2009) Org Biomol Chem 7:2669–2677

    Article  CAS  Google Scholar 

  32. Liu JM, Peng XG, Sun W, Zhao YW, Xia CG (2008) Org Lett 10:3933–3936

    Article  CAS  Google Scholar 

  33. Xuan SH, Jiang WQ, Gong XL (2011) Dalton Trans 40:7827–7830

    Article  CAS  Google Scholar 

  34. Du Q, Zhang W, Ma H, Zheng J, Zhou B, Li Y (2012) Tetrahedron 68:3577–3584

    Article  CAS  Google Scholar 

  35. Gawande MB, Rathi AK, Nogueira ID, Varma RS, Branco PS (2013) Green Chem 15:1895–1899

    Article  CAS  Google Scholar 

  36. Vaquer L, Riente P, Sala X, Jansat S, Benet-Buchholz J, Llobet A, Pericàs MA (2013) Catal Sci Technol 3:706–714

    Article  CAS  Google Scholar 

  37. Atashkar B, Rostami A, Tahmasbi B (2013) Catal Sci Technol 3:2140–2146

    Article  CAS  Google Scholar 

  38. Liu S, Ni Y, Yang J, Hu H, Ying A, Xu S (2014) Chin J Chem 32:343–348

    Article  CAS  Google Scholar 

  39. Sheykhan M, Ma’mani L, Ebrahimi A, Heydari A (2011) J Mol Catal A 335:253–261

    Article  CAS  Google Scholar 

  40. Xu HJ, Wan X, Shen YY, Xu S, Feng YS (2012) Org Lett 14:1210–1213

    Article  CAS  Google Scholar 

  41. Gawande MB, Bonifacío VDB, Varma RS, Nogueira ID, Bundaleski N, Ghumman CAA, Teodoro OMND, Branco PS (2013) Green Chem 15:1226–1231

    Article  CAS  Google Scholar 

  42. Du W, Xia S, Nie R, Hou Z (2014) Ind Eng Chem Res 53:4589–4594

    Article  CAS  Google Scholar 

  43. Riente P, Mendoza C, Pericás MA (2011) J Mater Chem 21:7350–7355

    Article  CAS  Google Scholar 

  44. Sobhani S, Bazrafshan M, Delluei AA, Parizi ZP (2013) Appl Catal A 454:145–151

    Article  CAS  Google Scholar 

  45. Leadbeater NE, Marco M (2002) Chem Rev 102:3217–3274

    Article  CAS  Google Scholar 

  46. Minakata S, Komatsu M (2009) Chem Rev 109:711–724

    Article  CAS  Google Scholar 

  47. Kong Y, Tan R, Zhao L, Yin D (2013) Green Chem 15:2422–2433

    Article  CAS  Google Scholar 

  48. Ying A, Liu S, Ni Y, Qiu F, Xu S, Tang W (2014) Catal Sci Technol 4:2115–2125

    Article  CAS  Google Scholar 

  49. Ying A, Xu S, Liu S, Ni Y, Yang J, Wu C (2014) Ind Eng Chem Res 53:547–552

    Article  CAS  Google Scholar 

  50. Ying A, Ni Y, Xu S, Liu S, Yang J, Li R (2014) Ind Eng Chem Res 53:5678–5682

    Article  CAS  Google Scholar 

  51. Sharghi H, Ebrahimpourmoghaddam S, Doroodmand MM (2013) Tetrahedron 69:4708–4724

    Article  CAS  Google Scholar 

  52. Kulkarni MA, Pandurangi VR, Desai UV, Wadgaonkar PP (2012) C R Chim 15:745–752

    Article  CAS  Google Scholar 

  53. Dar BA, Pandey N, Singh S, Bamezai RK, Sharma M, Vishwakarma RA, Singh B (2014) Tetrahedron Lett 55:623–628

    Article  CAS  Google Scholar 

  54. Nishioa K, Ikedaa M, Gokonb N, Tsubouchi S, Narimatsua H, Mochizuki Y, Sakamotoa S, Sandhuc A, Abe M, Handa H (2007) J Magn Magn Mater 310:2408–2410

    Article  Google Scholar 

  55. Deng YH, Qi DW, Deng CH, Zhang XM, Zhao DY (2008) J Am Chem Soc 130:28–29

    Article  CAS  Google Scholar 

  56. Zhang Y, Zhao Y, Xia C (2009) J Mol Catal A 306:107–112

    Article  CAS  Google Scholar 

  57. Bordoloi A, Sahhoo S, Lefebvre F, Halligudi SB (2008) J Catal 259:232–239

    Article  CAS  Google Scholar 

  58. Cabrera L, Gutierrez S, Morales MP, Menendez N, Herrasti P (2009) J Magn Magn Mater 321:2115–2120

    Article  CAS  Google Scholar 

  59. Lombardo M, Trombini C (2010) ChemCatChem 2:135–145

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful for the financial supports for this research by the National Natural Science Foundation of China (Grant 21106090, 21176170, and 21272169), and Zhejiang Provincial Natural Science Foundation of China (No. LY12B02004).

Author information

Authors and Affiliations

  1. School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, People’s Republic of China

    Zhifeng Li, Yuxiang Ni & Songlin Xu

  2. School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou, 318000, People’s Republic of China

    Fangli Qiu, Anguo Ying & Yunlong Wang

Authors
  1. Zhifeng Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yuxiang Ni
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Fangli Qiu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Anguo Ying
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Songlin Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yunlong Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Anguo Ying or Songlin Xu.

Electronic Supplementary Material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 7396 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li, Z., Ni, Y., Qiu, F. et al. Novel Ionic Tagged Amine Anchored on Magnetic Nanoparticles: An Efficient and Magnetically Recyclable Catalyst for Phospha-Michael Addition. Catal Lett 144, 1810–1818 (2014). https://doi.org/10.1007/s10562-014-1342-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-014-1342-1

Keywords

Search

Navigation