Skip to main content
SpringerLink
Log in

Direct access to β-seleno sulfones at room temperature through selenosulfonylation of alkenes

  • Communications
  • Published:
Science China Chemistry Aims and scope Submit manuscript

Abstract

A new protocol has been developed for the formation of C−Se and C−S bonds by the direct selenosulfonylation of alkenes. This protocol is operationally simplistic, has a wide substrate scope, uses readily available seleno and sulfonyl sources, and is amenable to gram-scale synthesis. This reaction represents a significant addition to the limited number of reactions available for the intermolecular selenide difunctionalization of alkenes and would be useful for the synthesis of sulfur- and selenium-containing molecules

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. Mugesh G, du Mont WW, Sies H. Chem Rev, 2001, 101: 2125–2180

    Article  CAS  Google Scholar 

  2. Mugesh G, Singh HB. Acc Chem Res, 2002, 35: 226–236

    Article  CAS  Google Scholar 

  3. Nogueira CW, Zeni G, Rocha JBT. Chem Rev, 2004, 104: 6255–6286

    Article  CAS  Google Scholar 

  4. Rhoden CRB, Zeni G. Org Biomol Chem, 2011, 9: 1301–1313

    Article  CAS  Google Scholar 

  5. Paulmier C. Selenium Reagents and Intermediates in Organic Synthesis. Organic Chemistry Series. Oxford, U.K.: Pergamon, 1986

    Google Scholar 

  6. Freudendahl DM, Santoro S, Shahzad SA, Santi C, Wirth T. Angew Chem Int Ed, 2009, 48: 8409–8411

    Article  CAS  Google Scholar 

  7. Derek WJ, Risto L. Selenium and Tellurium Chemistry: from Small Molecules to Biomolecules and Materials. Berlin: Springer-Verlag, 2011

    Google Scholar 

  8. Zeni G, Larock RC. Chem Rev, 2004, 104: 2285–2310

    Article  CAS  Google Scholar 

  9. Jensen KH, Sigman MS. Org Biomol Chem, 2008, 6: 4083–4088c

    Article  CAS  Google Scholar 

  10. McDonald RI, Liu G, Stahl SS. Chem Rev, 2011, 111: 2981–3019

    Article  CAS  Google Scholar 

  11. Cardona F, Goti A. Nat Chem, 2009, 1: 269–275

    Article  CAS  Google Scholar 

  12. Wang Y, Zhang L, Yang Y, Zhang P, Du Z, Wang C. J Am Chem Soc, 2013, 135: 18048–18051

    Article  CAS  Google Scholar 

  13. Zhou B, Ma P, Chen H, Wang C. Chem Commun, 2014, 50: 14558–14561

    Article  CAS  Google Scholar 

  14. Ciesielski J, Dequirez G, Retailleau P, Gandon V, Dauban P. Chem Eur J, 2016, 22: 9338–9347

    Article  CAS  Google Scholar 

  15. Courant T, Masson G. J Org Chem, 2016, 81: 6945–6952 and references therein

    Article  CAS  Google Scholar 

  16. Ivachtchenko AV, Golovina ES, Kadieva MG, Kysil VM, Mitkin OD, Tkachenko SE, Okun IM. J Med Chem, 2011, 54: 8161–8173

    Article  CAS  Google Scholar 

  17. Huang Y, Huo L, Zhang S, Guo X, Han CC, Li Y, Hou J. Chem Commun, 2011, 47: 8904–8906c

    Article  CAS  Google Scholar 

  18. Kamigata N, Narushima T, Sawada H, Kobayashi M. Bull Chem Soc Jpn, 1984, 57: 1421–1422

    Article  CAS  Google Scholar 

  19. Lu Q, Zhang J, Wei F, Qi Y, Wang H, Liu Z, Lei A. Angew Chem Int Ed, 2013, 52: 7156–7159

    Article  CAS  Google Scholar 

  20. Huo C, Wang Y, Yuan Y, Chen F, Tang J. Chem Commun, 2016, 52: 7233–7236

    Article  CAS  Google Scholar 

  21. Taniguchi N. J Org Chem, 2015, 80: 7797–7802

    Article  CAS  Google Scholar 

  22. Wan X, Sun K, Zhang G. Sci China Chem, 2017, 60: doi: 10.1007/s11426-016-0284-2

  23. Back TG, Collins S. J Org Chem, 1981, 46: 3249–3256

    Article  CAS  Google Scholar 

  24. Black KA, Vogel P. J Org Chem, 1986, 51: 5341–5348

    Article  CAS  Google Scholar 

  25. Gancarz RA, Kice JL. J Org Chem, 1981, 46: 4899–4906

    Article  CAS  Google Scholar 

  26. Bäckvall JE, Nájera C, Yus M. Tetrahedron Lett, 1988, 29: 1445–1448

    Article  Google Scholar 

  27. Sun K, Wang X, Lv Y, Li G, Jiao H, Dai C, Li Y, Zhang C, Liu L. Chem Commun, 2016, 52: 8471–8474

    Article  CAS  Google Scholar 

  28. Sun K, Li Y, Xiong T, Zhang J, Zhang Q. J Am Chem Soc, 2011, 133: 1694–1697

    Article  CAS  Google Scholar 

  29. Sun K, Wang X, Li G, Zhu Z, Jiang Y, Xiao B. Chem Commun, 2014, 50: 12880–12883

    Article  CAS  Google Scholar 

  30. Sun K, Wang X, Liu L, Sun J, Liu X, Li Z, Zhang Z, Zhang G. ACS Catal, 2015, 5: 7194–7198

    Article  CAS  Google Scholar 

  31. Sun K, Li Y, Zhang Q. Sci China Chem, 2015, 58: 1354–1358

    Article  CAS  Google Scholar 

  32. Sun K, Lv Y, Wang J, Sun J, Liu L, Jia M, Liu X, Li Z, Wang X. Org Lett, 2015, 17: 4408–4411

    Article  Google Scholar 

  33. Yanagisawa S, Ueda K, Taniguchi T, Itami K. Org Lett, 2008, 10: 4673–4676

    Article  CAS  Google Scholar 

  34. Liu W, Cao H, Zhang H, Zhang H, Chung KH, He C, Wang H, Kwong FY, Lei A. J Am Chem Soc, 2010, 132: 16737–16740

    Article  CAS  Google Scholar 

  35. Sun CL, Li H, Yu DG, Yu M, Zhou X, Lu XY, Huang K, Zheng SF, Li BJ, Shi ZJ. Nat Chem, 2010, 2: 1044–1049

    Article  CAS  Google Scholar 

  36. Li X, Xu X, Hu P, Xiao X, Zhou C. J Org Chem, 2013, 78: 7343–7348

    Article  CAS  Google Scholar 

  37. Shen T, Yuan Y, Song S, Jiao N. Chem Commun, 2014, 50: 4115

    Article  CAS  Google Scholar 

  38. Wei W, Wen J, Yang D, Du J, You J, Wang H. Green Chem, 2014, 16: 2988–2991

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the National Natural Science Foundation of China (U1504210), the China Postdoctoral Science Foundation (2015M572110), and Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis (130028651).

Author information

Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang, 455000, China

    Kai Sun, Yunhe Lv, Zuodong Shi, Fangfang Fu & Chong Zhang

  2. Henan Province Key Laboratory of New Opto-Electronic Functional Materials, Anyang, 455000, China

    Kai Sun

  3. School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007, China

    Zhiguo Zhang

Authors
  1. Kai Sun
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yunhe Lv
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zuodong Shi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Fangfang Fu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Chong Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Zhiguo Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Kai Sun or Zhiguo Zhang.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sun, K., Lv, Y., Shi, Z. et al. Direct access to β-seleno sulfones at room temperature through selenosulfonylation of alkenes. Sci. China Chem. 60, 730–733 (2017). https://doi.org/10.1007/s11426-016-0412-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-016-0412-0

Keywords

Search

Navigation