Skip to main content
Log in

Selective N-Alkylation of Aromatic Primary Amines Catalyzed by Bio-catalyst or Deep Eutectic Solvent

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Biocatalysts or deep eutectic solvents (DES) are effective for selective N-alkylation of various aromatic primary amines. These methods avoided complexity of multiple alkylations giving products in good yields. Both DES and lipase can be recycled and re-used at least five times. In addition, these catalysts are biodegradable, non-toxic and cost-effective.

Graphical 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.

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Fig. 1

Similar content being viewed by others

References

  1. Seayad AMA, Klein H, Jackstell R, Gross T, Beller M (2002) Science 297:1676

    Article  CAS  Google Scholar 

  2. Bhattcharyya AK, Nandi DK (1975) lnd Eng Chem Prod Res Dev 14:162

    Article  Google Scholar 

  3. Pillai RBC (1993) J Mol Catal 84:125

    Article  CAS  Google Scholar 

  4. Bradshaw JS, Krakowiak KE, Izatt RM (1992) Tetrahedron 48:4475

    Article  CAS  Google Scholar 

  5. Bergeron RJ, Feng Y, Weimar WR, McManis JS, Dimova H, Porter C, Raisler B, Phanstiel O (1997) J Med Chem 40:1475

    Article  CAS  Google Scholar 

  6. Szardenings AK, Burkoth TS, Look GC, Campbell DA (1996) J Org Chem 61:6720

    Article  CAS  Google Scholar 

  7. Koh K, Ben RN, Durts T (1993) Tetrahedron Lett 34:4473

    Article  CAS  Google Scholar 

  8. Salvatore RN, Nagle AS, Jung KW (2002) J Org Chem 67:674

    Article  CAS  Google Scholar 

  9. Won KJ, Kazuya Y, Noritaka M (2009) J Catal 263:205

    Article  Google Scholar 

  10. Benoit B, Stefan M, Rhett K (2009) Chem Eur J 15:3790

    Article  Google Scholar 

  11. Schmid A, Dordick JS, Hauer B, Kiener A, Wubbolts M, Witholt B (2001) Nature 409:258

    Article  CAS  Google Scholar 

  12. Kiran KR, Divakar S (2001) J Biotechnol 87:109

    Article  CAS  Google Scholar 

  13. Yadav GD, Manjula Devi K (2004) Chem Eng Sci 59:373

    Article  CAS  Google Scholar 

  14. Therisod M, Klibanov AM (1987) J Am Chem Soc 109:3977

    Article  CAS  Google Scholar 

  15. Zhang LQ, Zhang YD, Xu L, Li XL, Yang XC, Xu GL (2001) Enzym Microb Technol 29:129

    Article  CAS  Google Scholar 

  16. Abbott AP, Davies DL, Capper G, Rasheed RK, Tambyrajah V (2007) US Patent 7,183,433

  17. Abbott AP, Capper G, Davies DL, Rasheed RK, Tambyrajah V (2003) Chem Commun 1:70

  18. Gorke JT, Srienc F, Kazlauskas RJ (2008) Chem Commun 10:1235

  19. Jhong H, Wong D, Wan C, Wang Y, Wei T (2009) Electrochem Commun 11:209

    Article  CAS  Google Scholar 

  20. Abbott AP, Capper G, McKenzie KJ, Ryder KS (2007) J Electroanal Chem 599:288

    Article  CAS  Google Scholar 

  21. Abbott AP, Bell TJ, Handa S, Stoddart B (2005) Green Chem 7:705

    Article  CAS  Google Scholar 

  22. Morales RC, Tambyrajah V, Jenkins PR, Davies DL, Abbott AP (2004) Chem Commun 2:158

  23. Sonawane YA, Phadtare SB, Borse BN, Jagtap AR, Shankarling GS (2010) Org Lett 12:1456

    Article  CAS  Google Scholar 

  24. Li C, Feng X, Wang N, Zhou Y, Yu X (2008) Green Chem 10:616

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Authors are thankful to UGC-CAS for providing fellowship and Institute of Chemical Technology, SAIF IIT—Bombay and Institute of Science, Mumbai for recording 1H NMR, IR and Mass spectra.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ganapati Shankarling.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Singh, B., Lobo, H. & Shankarling, G. Selective N-Alkylation of Aromatic Primary Amines Catalyzed by Bio-catalyst or Deep Eutectic Solvent. Catal Lett 141, 178–182 (2011). https://doi.org/10.1007/s10562-010-0479-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-010-0479-9

Keywords

Navigation