Skip to main content
Log in

Cu-ACP-Am-Fe3O4@SiO2: an efficient and recyclable heterogeneous catalyst for the Chan–Lam coupling reaction of boronic acids and amines

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

We have developed an efficient method for Cu-ACP-Am-Fe3O4@SiO2 catalyzed Chan–Lam coupling of phenylboronic acid with primary amine furnished secondary amines. The catalyst offered virtues like mild reaction conditions, magnetically separable, and reusable and exhibits excellent performance in terms of good product yield and high turnover number.

Graphic abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Hartwig JF (2008) Nature 455:314

    Article  CAS  Google Scholar 

  2. Beccalli EM, Broggini G, Martinelli M, Sottocornola S (2007) Chem Rev 107:5318

    Article  CAS  Google Scholar 

  3. Monnier F, Taillefer MM (2009) Angew Chem Int Ed 48:6954

    Article  CAS  Google Scholar 

  4. Lam PYS, Clark CG, Saubern S, Adams J, Winters MP, Chan DMT, Combs A (1998) Tetrahedron Lett 39:2941

    Article  CAS  Google Scholar 

  5. Vantourout JC, Law RP, Isidro-Llobet A, Atkinson SJ, Watson AJB (2016) J Org Chem 81:3942

    Article  CAS  Google Scholar 

  6. Onaka T, Umemoto H, Miki Y, Nakamura A, Maegawa T (2014) J Org Chem 79:6703

    Article  CAS  Google Scholar 

  7. Huang F, Quach TD, Batey RA (2013) Org Lett 15:3150

    Article  CAS  Google Scholar 

  8. Zhang J, Jia RP, Wang DH (2016) Tetrahedron Lett 57:3604

    Article  CAS  Google Scholar 

  9. Reddy AS, Reddy KR, Rao DN, Jaladanki CK, Bharatam PV, Lam PYS, Das P (2017) Org Biomol Chem 15:801

    Article  Google Scholar 

  10. Vantourout JC, Miras HN, Isidro-Llobet A, Sproules S, Watson AJB (2017) J Am Chem Soc 139:4769

    Article  CAS  Google Scholar 

  11. Baruah J, Gogoi K, Dewan A, Borah G, Bora U (2017) Bull Korean Chem Soc 38:1203

    Article  CAS  Google Scholar 

  12. Li B, Li M, Yao C, Shi Y, Ye D, Wu J, Zhao D (2013) J Mater Chem A 1:6742

    Article  CAS  Google Scholar 

  13. Moghaddam FM, Pourkaveh R, Gholamtajari M (2018) Appl Organomet Chem 32:4568

    Article  Google Scholar 

  14. Hu A, Yee GT, Lin WJ (2005) Am Chem Soc 127:12486

    Article  CAS  Google Scholar 

  15. Abu-Reziq R, Alper H, Wang D, Post ML (2006) J Am Chem Soc 128:5279

    Article  CAS  Google Scholar 

  16. Dalaigh CO, Corr SA, Gun’ko Y, Connon SJ (2007) Angew Chem Int Ed 46:4329

    Article  CAS  Google Scholar 

  17. Bohara RA, Thorat ND, Pawar SH (2016) RSC Adv 6:43989

    Article  CAS  Google Scholar 

  18. Cano R, Yus M, Ramon DJ (2012) Tetrahedron 68:1393

    Article  CAS  Google Scholar 

  19. Vibhute SP, Mhaldar PM, Gaikwad DS, Shejawal RV, Pore DM (2018) Tetrahedron Lett 59:3652

    Article  Google Scholar 

  20. Mane MM, Korade SN, Chinchkar SM, Pore DM (2018) Org Prep Proced Int 50:454

    Article  CAS  Google Scholar 

  21. Chan DMT, Monaco KL, Wang RP, Winters MP (1998) Tetrahedron Lett 39:2933

    Article  CAS  Google Scholar 

  22. Bekolo H (2007) J Can Chem 85:42

    Article  CAS  Google Scholar 

  23. Shieh FK, Wang SC, Yen C, Wu C, Dutta S, Chou LY, Morabito JV, Hu P, Hsu MH, Wu KCW, Tsung CK (2015) J Am Chem Soc 137:4276

    Article  CAS  Google Scholar 

  24. Chen S, Huang H, Liu X, Shen J, Jiang H, Liu H (2008) Comb Chem 10:358

    Article  CAS  Google Scholar 

  25. Singh BK, Appukkuttan P, Claerhout S, Parmar VS, Van der Eycken E (2006) Org Lett 8:1863

    Article  CAS  Google Scholar 

  26. Wentzel MT, Hewgley JB, Kamble RM, Wall PD, Kozlowski MC (2009) Adv Synth Catal 351:931

    Article  CAS  Google Scholar 

  27. Moon SY, Nam J, Rathwell K, Kim WS (2014) Org Lett 16:338

    Article  CAS  Google Scholar 

  28. Duan X, Liu N, Liu K, Song Y, Wang J, Mao X, Xu W, Yang S, Li H, Ma J (2018) Tetrahedron Lett 59:4187

    Article  CAS  Google Scholar 

  29. Sharma H, Mahajan H, Jamwal B, Paul S (2018) Catal Commun 107:68

    Article  CAS  Google Scholar 

  30. Dutta MM, Phukan P (2018) Catal Commun 109:38

    Article  CAS  Google Scholar 

  31. Khosravi A, Mokhtari J, Naimi-Jamal MR, Tahmasebi S, Panahi L (2017) RSC Adv 7:46022

    Article  CAS  Google Scholar 

  32. Han Y, Zhang M, Zhang YQ, Zhang ZH (2018) Green Chem 20:4891

    Article  CAS  Google Scholar 

Download references

Acknowledgements

One of the authors, DMP, is grateful to acknowledge Shivaji University, Kolhapur for financial assistance through Research Strengthening Scheme [SU/C&U.D.Section/89/1386].

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Dattaprasad M. Pore.

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 291 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vibhute, S.P., Mhaldar, P.M., Gaikwad, D.S. et al. Cu-ACP-Am-Fe3O4@SiO2: an efficient and recyclable heterogeneous catalyst for the Chan–Lam coupling reaction of boronic acids and amines. Monatsh Chem 151, 87–92 (2020). https://doi.org/10.1007/s00706-019-02529-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-019-02529-w

Keywords

Navigation