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4-Vinylbenzyl-substituted silver(I) N-heterocyclic carbene complexes and ruthenium(II) N-heterocyclic carbene complexes: synthesis and transfer hydrogenation of ketones

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Abstract

4-Vinylbenzyl-substituted Ag(I) N-heterocyclic carbene (NHC) complexes and Ru(II) NHC complexes have been synthesized. The Ag(I) complexes were synthesized from the imidazolium salts and Ag2O in dichloromethane at room temperature. The Ru(II) complexes were prepared from Ag(I) NHC complexes by transmetallation. The six 4-Vinylbenzyl-substituted Ag(I) NHC complexes and six 4-Vinylbenzyl-substituted Ru(II) NHC complexes have been characterized by spectroscopic techniques and elemental analyses. The Ru(II) NHC complexes show catalytic activity for the transfer hydrogenation of ketones.

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References

  1. Herrmann WA (2002) Angew Chem Int Ed 41:1290

    Article  CAS  Google Scholar 

  2. Poyatos M, Mata JA, Peris E (2009) Chem Rev 109:3677

    Article  CAS  Google Scholar 

  3. Diez-Gonzalez S, Marion N, Nolan SP (2009) Chem Rev 109:3612

    Article  CAS  Google Scholar 

  4. Huang J, Stevens ED, Nolan SP, Petersen JL (1999) J Am Chem Soc 121:2674

    Article  CAS  Google Scholar 

  5. Huang J, Schanz H-J, Stevens ED, Nolan SP (1999) Organometallics 18:2370

    Article  CAS  Google Scholar 

  6. Hillier AC, Sommer WJ, Yong BS, Petersen JL, Cavallo L, Nolan SP (2003) Organometallics 22:4322

    Article  CAS  Google Scholar 

  7. Crabtree RH (2005) J Organomet Chem 690:5451

    Article  CAS  Google Scholar 

  8. Diez-Gonzalez S, Nolan SP (2007) Coord Chem Rev 251:874

    Article  CAS  Google Scholar 

  9. Liddle ST, Edworthy IS, Arnold PL (2007) Chem Soc Rev 36:1732

    Article  CAS  Google Scholar 

  10. Lee HM, Lee CC, Cheng PY (2007) Curr Org Chem 11:1491

    Article  CAS  Google Scholar 

  11. Normand AT, Cavell KJ (2008) Eur J Inorg Chem 2008:2781

    Article  Google Scholar 

  12. Poyatos M, Mata JA, Peris E (2009) Chem Rev 109:3677

    Article  CAS  Google Scholar 

  13. Cui XH, Burgess K (2005) Chem Rev 105:3272

    Article  CAS  Google Scholar 

  14. Nanchen S, Pfaltz A (2006) Chem Eur J 12:4550

    Article  CAS  Google Scholar 

  15. Chen D, Banphavichit V, Reibenspies J, Burgess K (2007) Organometallics 26:855

    Article  CAS  Google Scholar 

  16. Horn S, Albrecht M (2011) Chem Commun 47:8802

    Article  CAS  Google Scholar 

  17. Horn S, Gandolfi C, Albrecht M (2011) Eur J Inorg Chem 2011:2863

    Article  CAS  Google Scholar 

  18. Corberán R, Sanaú M, Peris E (2007) Organometallics 26:3492

    Article  Google Scholar 

  19. Zeng FL, Yu ZK (2008) Organometallics 27:6025

    Article  CAS  Google Scholar 

  20. Dyson G, Frison JC, Whitwood AC, Douthwaite RE (2009) Dalton Trans 2009:7141–7151

    Article  Google Scholar 

  21. Gnanamgari D, Sauer ELO, Schley ND, Butler C, Incarvito CD, Crabtree RH (2009) Organometallics 28:321

    Article  CAS  Google Scholar 

  22. Cross WB, Daly CG, Boutadla Y, Singh K (2011) Dalton Trans 40:9722

    Article  CAS  Google Scholar 

  23. Del Pozo C, Iglesias M, Sánchez F (2011) Organometallics 30:2180

    Article  Google Scholar 

  24. Jimenez MV, Fernandez-Tornos J, Perez-Torrente JJ, Modrego FJ, Winterle S, Cunchillos C, Lahoz FJ, Oro LA (2011) Organometallics 30:5493

    Article  CAS  Google Scholar 

  25. Hahn FE, Jahnke MC (2008) Angew Chem Int Ed 47:3122

    Article  CAS  Google Scholar 

  26. Diez-Gonzalez S, Marion N, Nolan SP (2009) Chem Rev 109:3612

    Article  CAS  Google Scholar 

  27. Garrison JC, Youngs W (2005) J Chem Rev 105:3978

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  29. Lin IJB, Vasam CS (2004) Commun Inorg Chem 25:75

    Article  CAS  Google Scholar 

  30. Herrmann WA (2002) Angew Chem Int Ed 41:1290

    Article  CAS  Google Scholar 

  31. Perry MC, Burgess K (2003) Tetrahedron Assymetry 14:951

    Article  CAS  Google Scholar 

  32. Dragutan I, Dragutan V, Delaude L, Demonceau A (2005) ARKIVOC 10:206

    Article  Google Scholar 

  33. Yigit B, Yigit M, Ozdemir I, Cetinkaya E (2012) Transit Met Chem 37:297

    Article  CAS  Google Scholar 

  34. Wwn O, Lough AJ, Morris RH (2010) Chem Commun 46:8240

    Article  Google Scholar 

  35. Ding N, Hor TSA (2010) Dalton Trans 39:10179

    Article  CAS  Google Scholar 

  36. Dragutan V, Dragutan I, Delaude L, Demonceau A (2007) Coord Chem Rev 251:765

    Article  CAS  Google Scholar 

  37. Nayori R (1994) Asymmetric catalysis in organic synthesis. Wiley, New York

    Google Scholar 

  38. I Ojima (2000) Catalytic asymmetric synthesis, 2nd edition, Wiley, New York

  39. Gürbüz N, Özcan EÖ, Özdemir İ, Çetinkaya B, Şahin O, Büyükgüngör O (2012) Dalton Trans 41:2330

    Article  Google Scholar 

  40. Noyori R, Hashiguchi S (1997) Acc Chem Res 30:97

    Article  CAS  Google Scholar 

Download references

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Correspondence to Aydın Aktaş.

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Aktaş, A., Gök, Y. 4-Vinylbenzyl-substituted silver(I) N-heterocyclic carbene complexes and ruthenium(II) N-heterocyclic carbene complexes: synthesis and transfer hydrogenation of ketones. Transition Met Chem 39, 925–931 (2014). https://doi.org/10.1007/s11243-014-9877-y

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