Skip to main content
SpringerLink
Log in

Ruthenium(II)-NHC-catalyzed (NHC = perhydrobenzimidazol-2-ylidene) alkylation of amines using the hydrogen borrowing methodology under solvent-free conditions

  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Abstract

New ruthenium(II) complexes with N-heterocyclic carbene ligand were synthesized by transmetalation reactions between silver(I) N-heterocyclic carbene complexes and [RuCl2(p-cymene)]2. The complexes were characterized by physicochemical and spectroscopic methods. These ruthenium complexes were applied to the N-monoalkylation of aromatic amines with a wide range of primary alcohols under solvent-free conditions using the hydrogen borrowing strategy. The catalytic reactions using all ruthenium complexes resulted in N-monoalkylated products with high selectivities using furfuryl alcohol as the alkylating agent.

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
Scheme 2

Similar content being viewed by others

References

  1. Ricci A (2008) Amino group chemistry: from synthesis to the life sciences. Wiley-VCH, Weinheim

    Google Scholar 

  2. Salvatore RN, Yoon CH, Jung KW (2001) Tetrahedron 57:7785

    Article  CAS  Google Scholar 

  3. Storer RI, Carrera DE, Ni Y, MacMillan DWC (2006) J Am Chem Soc 128:84

    Article  CAS  PubMed  Google Scholar 

  4. Hartwig JF (1998) Angew Chem Int Ed Engl 37:2046

    Article  CAS  PubMed  Google Scholar 

  5. Hannedouche J, Schulz E (2013) Chem Eur J 19:4972

    Article  CAS  PubMed  Google Scholar 

  6. Moballigh A, Seayad A, Jackstell R, Beller M (2003) J Am Chem Soc 125:10311

    Article  CAS  Google Scholar 

  7. Guillena G, Ramon DJ, Yus M (2010) Chem Rev 110:1611

    Article  CAS  PubMed  Google Scholar 

  8. Yang Q, Wang Q, Yu Z (2015) Chem Soc Rev 44:2305

    Article  CAS  PubMed  Google Scholar 

  9. Corma A, Navas J, Sabater MJ (2018) Chem Rev 118:1410

    Article  CAS  PubMed  Google Scholar 

  10. Saidi O, Blacker AJ, Farah MM, Marsden SP, Williams JMJ (2009) Angew Chem Int Ed 48:7375

    Article  CAS  Google Scholar 

  11. Corma A, Navas J, Rodenas T, Sabater MJ (2013) Chem Eur J 19:17464

    Article  CAS  PubMed  Google Scholar 

  12. Grigg R, Mitchell TRB, Sutthivaiyakit S, Tongpenyai N (1981) J Chem Soc Chem Commun 12:611

    Article  Google Scholar 

  13. Watanabe Y, Tsuji Y, Ohsugi Y (1981) Tetrahedron Lett 22:2667

    Article  CAS  Google Scholar 

  14. Hamid MHSA, Allen CL, Lamb GW, Maxwell AC, Maytum HC, Watson AJA, Williams JMJ (2009) J Am Chem Soc 131:1766

    Article  CAS  PubMed  Google Scholar 

  15. Saidi O, Blacker AJ, Farah MM, Marsden SP, Williams JMJ (2010) Chem Commun 46:1541

    Article  CAS  Google Scholar 

  16. Llabres-Campaner PJ, Ballesteros-Carrido R, Ballesteros R, Abarde B (2017) Tetrahedron 73:5552

    Article  CAS  Google Scholar 

  17. Liu H, Chuah GK, Jaenicke S (2012) J Catal 191:130

    Article  CAS  Google Scholar 

  18. Quintrad A, Rodrigez J (2016) Chemsuschem 9:28

    Article  CAS  Google Scholar 

  19. Santoro F, Psaro R, Ravasio N, Zaccherio F (2014) RSC Adv 4:2596

    Article  CAS  Google Scholar 

  20. Wong MC, Peterson MB, Pernik I, McBurney RT, Messerle BA (2017) Inorg Chem 56:14682

    Article  CAS  PubMed  Google Scholar 

  21. Huang R, Yang Y, Wang DS, Zhang L, Wang D (2018) Org Chem Front 5:203

    Article  CAS  Google Scholar 

  22. Montgomery SL, Mangas-Sanchez J, Thompson MP, Aleku GA, Dominguez B, Turner NJ (2017) Angew Chem Int Ed 56:10491

    Article  CAS  Google Scholar 

  23. Jansenn-Müller D, Glorius F (2017) Chem Soc Rev 46:4845

    Article  Google Scholar 

  24. De Fremont P, Marion N, Nolan SP (2009) Coord Chem Rev 253:862

    Article  CAS  Google Scholar 

  25. Liu W, Gust R (2013) Chem Soc Rev 42:755

    Article  CAS  PubMed  Google Scholar 

  26. Mercs L, Albrecht M (2010) Chem Soc Rev 39:1903

    Article  CAS  PubMed  Google Scholar 

  27. Diez-Gonzalez S (2007) N-heterocyclic carbenes. Royal Society of Chemistry, Cambridge

    Google Scholar 

  28. Buil ML, Esteruelas MA, Herrero J, Izquierdo S, Pastor IM, Yus M (2013) ACS Catal 3:2072

    Article  CAS  Google Scholar 

  29. Dam JH, Osztrovszky G, Nordstrom LU, Madsen R (2010) Chem Eur J 16:6820

    Article  CAS  PubMed  Google Scholar 

  30. Fujita K, Furukawa S, Morishima N, Shimizu MS, Yamaguchi R (2018) ChemCatChem 10:1993

    Article  CAS  Google Scholar 

  31. Wong CM, McBurney RT, Binding SC, Peterson MB, Goncales VR, Gooding JJ, Messerle BA (2017) Green Chem 19:3142

    Article  CAS  Google Scholar 

  32. Prades A, Corberan R, Poyatos M, Peris E (2008) Chem Eur J 14:11474

    Article  CAS  PubMed  Google Scholar 

  33. Bartoszewich A, Marcos R, Sahoo S, Inge AK, Zou X, Martin-Matute B (2012) Chem Eur J 18:14510

    Article  CAS  Google Scholar 

  34. Marichev KO, Takacs JM (2016) ACS Catal 6:2205

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  35. Li JQ, Andersson PG (2013) Chem Commun 49:6131

    Article  CAS  Google Scholar 

  36. Shan SP, Xiaoke X, Gnanaprakasam B, Dang TT, Ramalingam B, Huynh HH, Seayad AM (2015) RSC Adv 5:4434

    Article  CAS  Google Scholar 

  37. Kaloğlu M, Gürbüz N, Semeril D, Özdemir İ (2018) Eur J Inorg Chem 1236

  38. Yigit M (2009) Molecules 14:2032

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  39. Özdemir İ, Yigit M, Çetinkaya E, Çetinkaya B (2006) Heterocycles 68:1371

    Article  Google Scholar 

  40. Yiğit M, Bayram G, Yiğit B, Özdemir İ (2013) Heterocycles 87:897

    Article  CAS  Google Scholar 

  41. Wang HMJ, Lin IJB (1998) Organometallics 17:972

    Article  CAS  Google Scholar 

  42. Yiğit B, Yiğit M, Özdemir İ, Çetinkaya E (2012) Transit Met Chem 37:297

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science and Art, Adıyaman University, 02040, Adıyaman, Turkey

    Murat Yiğit & Beyhan Yiğit

  2. Catalysis Research and Application Center, Inönü University, 44280, Malatya, Turkey

    Emine Özge Karaca, Nevin Gürbüz & İsmail Özdemir

  3. Department of Chemistry, Faculty of Science and Art, Inönü University, 44280, Malatya, Turkey

    Nevin Gürbüz & İsmail Özdemir

Authors
  1. Murat Yiğit
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Emine Özge Karaca
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Beyhan Yiğit
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Nevin Gürbüz
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. İsmail Özdemir
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Murat Yiğit.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yiğit, M., Karaca, E.Ö., Yiğit, B. et al. Ruthenium(II)-NHC-catalyzed (NHC = perhydrobenzimidazol-2-ylidene) alkylation of amines using the hydrogen borrowing methodology under solvent-free conditions. Transit Met Chem 44, 565–573 (2019). https://doi.org/10.1007/s11243-019-00313-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11243-019-00313-7

Search

Navigation