Skip to main content
SpringerLink
Log in

A Simple Metal Free Oxidation of Sulfide Compounds

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

This work reports simple, efficient, selective protocol for the oxidation of sulfide compounds. Various sulfides were selectively and completely converted into their corresponding sulfoxides and sulfones using H2O2 as an oxidant in presence of catalytic amount of caprylic acid. The reaction proceeds at room temperature to give sulfoxide and by increasing the reaction temperature to 50 °C, this system provides selective formation of sulfone with high conversion and excellent yields. Green, convenient, easy work-up, chemoselectivity, broad substrate scope and regeneration of catalyst are the important highlights of this protocol.

Graphical Abstract

Using H2O2 as an oxidant in presence of catalytic amount of caprylic acid various sulfides were selectively and completely converted into their corresponding sulfoxides and sulfones.

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
Fig. 1

Similar content being viewed by others

References

  1. Frenanez I, Khiar N (2003) Chem Rev 103:3651

    Article  Google Scholar 

  2. Munoza M, Romanellia G, Bottob IL, Cabelloa CI, Lamonierc C (2010) Appl Catal B 100:254

    Article  Google Scholar 

  3. Ghaemi A, Rayati S, Zakavi S, Safari N (2009) Appl Catal A 353:154

    Article  CAS  Google Scholar 

  4. Spencer CM, Faulds D (2000) Drugs 103:321

    Article  Google Scholar 

  5. Romanowski G (2013) J Mol Catal A Chem 368:137

    Article  Google Scholar 

  6. Mba M, Prins LJ, Zonta C, Cametti M, Valkonen A, Rissanen K, licini G (2010) Dalton Trans 39:7384

    Article  CAS  Google Scholar 

  7. Khurana JM, Nand B (2010) Can J Chem 88:906

    Article  CAS  Google Scholar 

  8. Alcon MJ, Corma A, Iglesias M, Sanchez F (2002) J Mol Catal A Chem 178:253

    Article  CAS  Google Scholar 

  9. Das R, Chakarborty D (2010) Tetrahedron Lett 51:6255

    Article  CAS  Google Scholar 

  10. Mandal M, Chakarborty D (2015) RSC Adv 5:12111

    Article  CAS  Google Scholar 

  11. Chen TH, Yuan ZB, Carver A, Zhang R (2014) Appl Catal A 478:275

    Article  CAS  Google Scholar 

  12. Bagherzadeh M, Latifi R, Tahsini L, Amini M (2008) Catal Commun 10:196

    Article  CAS  Google Scholar 

  13. Matteucci M, Bhalay G, Bradley M (2003) Org Lett 5:235

    Article  CAS  Google Scholar 

  14. Gao J, Guo H, Liu S, Wang M (2007) Tetrahedron Lett 48:8453

    Article  CAS  Google Scholar 

  15. Raju BR, Sarkar S, Reddy U C, Saikia AK (2009) J Mol Catal A Chem 308:169

    Article  Google Scholar 

  16. Jayaseeli AMI, Rajagopal S (2009) J Mol Catal A Chem 309:103

    Article  CAS  Google Scholar 

  17. Gunaratne HQN, McKervey MA, Feutren S, Finlay J, Boyd J (1998) Tetrahedron Lett 39:5655

    Article  CAS  Google Scholar 

  18. Mello R, Olmos A, Aragonés AA, Rodríguez AD, Núñez MEG, Asensio G (2010) Eur J Org Chem 32:6200

    Article  Google Scholar 

  19. Karmee SK, Greiner L, Kraynov A, Muller TE, Niemeijer B, Leitner W (2010) Chem Commun 46:6705

    Article  CAS  Google Scholar 

  20. Rostami A, Akradi J (2010) Tetrahedron Lett 51:3501

    Article  CAS  Google Scholar 

  21. Jafarpour M, Ghahramaninezhad M, Rezaeifard A (2014) New J Chem 38:2917

    Article  CAS  Google Scholar 

  22. Golchoubian H, Hosseinpoor F (2007) Molecules 12:304

    Article  CAS  Google Scholar 

  23. Gayakwad EM, Patil VV, Shankarling GS (2016) New J Chem 40:223:24.

    Google Scholar 

  24. Tumula VR, Bondwal S, Bisht P, Pendem C, Kumar J (2012) React Kinet Mech Cat 107:449

    Article  CAS  Google Scholar 

  25. Dai DY, Wang L, Chen Q, He MY (2014) J Chem Res 38:183

    Article  CAS  Google Scholar 

  26. Secci F, Arca M, Frongia A, Piras PP (2014) New J Chem 38:3622

    Article  CAS  Google Scholar 

  27. Bahrami K (2006) Tetrahedron Lett 47:2009

    Article  CAS  Google Scholar 

  28. Varma RS, Saini RK, Meshram HM (1997) Tetrahedron Lett 38:6525

    Article  CAS  Google Scholar 

  29. Rostami A, Tahmasbi B, Abedi F, Shokri Z (2013) J Mol Catal A Chem 378:200

    Article  CAS  Google Scholar 

  30. Islam SM, Roy AS, Mondal P, Tuhina K, Mobarak M, Mondal J (2012) Tetrahedron Lett 53:127

    Article  CAS  Google Scholar 

  31. Jereb M (2012) Green Chem 14:3047

    Article  CAS  Google Scholar 

  32. Wagh RB, Gund SH, Nagarkar JM (2016) J Chem Sci 128:1321

    Article  CAS  Google Scholar 

  33. Malkov AV, Derrien N, Barlog M, Kocovsky P (2014) Chem Eur J 20:4542

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The author (RBW) is greatly thankful to the UGC (University Grant Commission, India) for providing the junior research fellowship (JRF).

Author information

Authors and Affiliations

  1. Department of Chemistry, Institute of Chemical Technology, Matunga, Mumbai, 400019, India

    Ravindra B. Wagh & Jayashree M. Nagarkar

Authors
  1. Ravindra B. Wagh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jayashree M. Nagarkar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jayashree M. Nagarkar.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 675 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wagh, R.B., Nagarkar, J.M. A Simple Metal Free Oxidation of Sulfide Compounds. Catal Lett 147, 181–187 (2017). https://doi.org/10.1007/s10562-016-1932-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-016-1932-1

Keywords

Search

Navigation