Skip to main content
SpringerLink
Log in

The chemoselective N-Boc protection of amines in the presence of solid-supported perchloric acid as an efficient and reusable solid acid

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

Abstract

The chemoselective N-Boc protection of amines has been performed in the presence of catalytic amount of poly(4-vinylpyridinium) perchlorate at room temperature .and neat conditions. This new method has distinct advantages, including its excellent yields and short reaction times as well as being green in terms of avoiding the use of toxic catalysts and solvents. Furthermore, the catalyst can be reused and recycled several times without significant loss in its 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

Similar content being viewed by others

References

  1. Greene TW, Wuts PGM (1999) Protective groups in organic synthesis, 3rd edn. Wiley, New York, p 306

    Book  Google Scholar 

  2. Gregory MJ (1970) J Chem Soc B 1201

  3. Kocienski PJ (2004) Protecting groups, 3rd edn. Georg Thieme Verlag, Stuttgart

    Google Scholar 

  4. Sartori G, Ballani R, Bigi F, Bosica G, Maggi R, Right P (2004) Chem Rev 104:199

    Article  CAS  Google Scholar 

  5. Wuensch E (1974) In: Muller E, Bayer O, Meerwein H, Ziegler KE (eds) Houben-Weyl-Methods of organic Chemistry, vol 15/1, 4th edn. Georg Thieme Verlag, Stuttgart, Germany, p 46

    Google Scholar 

  6. Snieckus V (1990) Chem Rev 90:879

    Article  CAS  Google Scholar 

  7. Lamothe M, Perez M, Colovray-Gotteland V, Halazy S (1996) Synlett 507

  8. Basel Y, Hasners A (2000) J Org Chem 65:6368

    Article  CAS  Google Scholar 

  9. Lutz C, Lutz V, Knochel P (1998) Tetrahedron 54:6385

    Article  CAS  Google Scholar 

  10. Kelly TA, McNeil DW (1994) Tetrahedron Lett 35:9003

    Article  CAS  Google Scholar 

  11. Boger DL, McKie JA (1995) J Org Chem 60:1271

    Article  CAS  Google Scholar 

  12. Muchowski JM, Venuti MC (1980) J Org Chem 45:4798

    Article  CAS  Google Scholar 

  13. Heydari A, Hosseini SE (2005) Adv Synth Catal 347:1929

    Article  CAS  Google Scholar 

  14. Pandey RK, Dagade SP, Upadhaya RK, Dongare MK, Kumar P (2002) Arkivoc 7:28

    Article  Google Scholar 

  15. Sunitha S, Kanjilal S, Reddy SP, Prasad BN (2008) Tetrahedron Lett 49:2527

    Article  CAS  Google Scholar 

  16. Upadhyaya DJ, Barge A, Stefania R, Cravottoa G (2007) Tetrahedron Lett 48:8318

    Article  CAS  Google Scholar 

  17. Das B, Venkateswarlu K, Krishnaiah M, Holla H (2006) Tetrahedron Lett 47:7551

    Article  CAS  Google Scholar 

  18. Reddy MS, Narender M, Nageswar YVD, Rao KR (2006) Synlett 1110

  19. Khaksar S, Heydari A, Tajbakhsh M, Vahdat SM (2008) Tetrahedron Lett 49:3527

    Article  CAS  Google Scholar 

  20. Inahashi N, Matsumiya A, Sato T (2008) Synlett 294

  21. Heydari A, Shiroodi RK, Hamadi H, Esfandyari M, Pourayoubi M (2007) Tetrahedron Lett 48:5865

    Article  CAS  Google Scholar 

  22. Chankeshwara SV, Chakraborti AK (2006) Org Lett 8:3259

    Article  CAS  Google Scholar 

  23. Chaskar A, Yewale S, Langi B, Deokar H (2009) J Korean Chem Soc 53:422

    Article  CAS  Google Scholar 

  24. Vilaivan T (2006) Tetrahedron Lett 47:6739

    Article  CAS  Google Scholar 

  25. Choudhary D, Paul S, Gupta R, Clark JH (2006) Green Chem 8:479

    Article  CAS  Google Scholar 

  26. Ghorbani-Choghamarani A, Sardari S (2011) J Sulfur Chem 32:63

    Article  CAS  Google Scholar 

  27. Dalpozzo R, Bartoli G, Sambri L, Melchiorre P (2010) Chem Rev 110:3501

    Article  CAS  Google Scholar 

  28. Chakraborti AK, Singh B, Chankeshwara SV, Patel AR (2009) J Org Chem 74:5967

    Article  CAS  Google Scholar 

  29. Karimi B, Khalkhali M (2005) J Mol Catal A: Chem 232:113

    Article  CAS  Google Scholar 

  30. Niknam K, Saberi D, Sefat MN (2009) Tetrahedron Lett 50:4058

    Article  CAS  Google Scholar 

  31. Khaligh NG (2012) J Mol Catal A: Chem 363–364:90

    Article  Google Scholar 

  32. Khaligh NG, Shirini F (2013) Ultrason Sonochem 20:26

    Article  CAS  Google Scholar 

  33. Khaligh NG (2014) Chinese J Catal 35:329

    Article  CAS  Google Scholar 

  34. Bartoli G, Bosco M, Locatelli M, Marcantoni E, Massaccesi M (2004) Synlett 1794

  35. Schumacher JC (1960) Perchlorates: their properties, manufacture and uses. Reinhold, New York

    Google Scholar 

  36. Long JR (2002) Chem Health Saf 9:12

    Article  CAS  Google Scholar 

  37. Shirini F, Khaligh NG (2012) J Iran Chem Soc 9:495

    Article  CAS  Google Scholar 

  38. Shirini F, Khaligh NG, Jolodar OG (2013) J Iran Chem Soc 10:181

    Article  CAS  Google Scholar 

  39. Chankeshwara SV, Chakraborti AK (2006) Tetrahedron Lett 47:1087

    Article  CAS  Google Scholar 

  40. Sharma GVM, Reddy JJ, Lakshmi PS, Krishna PR (2004) Tetrahedron Lett 45:6963

    Article  CAS  Google Scholar 

Download references

Acknowledgments

I am grateful to the University of Guilan Research Council for partial support of this work.

Author information

Authors and Affiliations

  1. Research House of Professor Reza, Education Guilan Rasht, District 1, 41569‐17139, Rasht, Iran

    Nader Ghaffari Khaligh

  2. Department of Educational Chemistry, Research and Planning Organization, Tehran, Iran

    Hassan Hazarkhani

Authors
  1. Nader Ghaffari Khaligh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hassan Hazarkhani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nader Ghaffari Khaligh.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khaligh, N.G., Hazarkhani, H. The chemoselective N-Boc protection of amines in the presence of solid-supported perchloric acid as an efficient and reusable solid acid. Monatsh Chem 145, 1975–1980 (2014). https://doi.org/10.1007/s00706-014-1274-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-014-1274-x

Keywords

Search

Navigation