Oxidation of alcohols in the presence of poly(N-heterocyclic carbene) containing palladium

Document Type : Original Article

Authors

1 Department of Chemistry, Islamic Azad University, Arak Branch

2 Department of Chemistry, University of Isfahan, Iran

10.22036/cr.2022.348102.1187

Abstract

In the present work, oxidation of alcohols with hydrogen peroxide catalyzed by a poly(N-heterocyclic carbene) containing palladium id reported. In this manner, the nano silica particles were functionalized with 3-chloropropyl bromide. Then this functionalized silica nanoparticles were reacted with imidazole, pentaerythrithol tetrabromide, and 1-methyl imidazole, respectively. Finally, this nano material was reacted with PdCl2 to obtain a (PdII-NHCs)n@nSiO2. after, synthesis, this dendiritic polymer was characterized by different analytical techniques. This material was used as an efficient catalyst for oxidation of benzylic alcohols with hydrogen peroxide. In this manner, the reaction parameters such as catalyst amount and kind of solvent was optimized. all reactions were carried out at room temperature and the corresponding aldehydes were obtained in high yields. The mentioned catalyst is of high activity and reusability in the oxidation reactions and reused several times withous significant loss of its catalytic activity. On the other hand, only small amount of Pd was leached in the two first runs.

Graphical Abstract

Oxidation of alcohols in the presence of poly(N-heterocyclic carbene) containing palladium

Keywords


  1. M. Hudlicky, Oxidations in Organic Chemistry, ACS Monograph Series, American Chemical Society, Washington, DC, 1990.
  2. S. S. Stahl, Angew. Chem., Int. Ed., 2004, 43, 3400.
  3. K. M. Gligorich, M. S. Sigman, Chem. Commun., 2009, 3854.
  4. Y. Kong, L. Wen, H. Song, S. Xu, M. Yang, B. Liu, B. Wang, Organometallics 30 (2011) 153–159.
  5. Y. H. Chang, Z. Y. Liu, Y. H. Liu, S. M. Peng, J. T. Chen, S. T. Liu, Dalton Trans. 40 (2011) 489–494.
  6. T. Tu, H. Mao, C. Herbert, M.Z. Xu, K.H. Dotz, Chem. Commun. 46 (2010)7796–7798.

7  S. Gu, H. Xu, N. Zhang, W. Chen, Chem. Asian J. 5 (2010) 1677–1686.

  1. N. Marion, S. P. Nolan, Acc. Chem. Res. 41 (2008) 1440–1449.
  2. G. C. Fortman, S. P. Nolan, Chem. Soc. Rev. 40 (2011) 5151–5169.
  3. Z. Pahlevanneshan, M. Moghadam, V. Mirkhani, S. Tangestaninejad, I. Mohammadpoor‎‒‎‎Baltork, S. Rezaei, New J. Chem. 39 (2015) 9729‎‒‎‎9734.
  4. Z. Pahlevanneshan, M. Moghadam, V. Mirkhani, S. Tangestaninejad, I. Mohammadpoor‎‒‎‎Baltork, H. Loghmani‎‒‎‎Khouzani, J. Organomet. Chem. 809 (2016) 31‎‒‎‎37.
  5. M. Ghotbinejad, A. R. Khosropour, I. Mohammadpoor‎‒‎‎Baltork, M. Moghadam, S. Tangestaninejad, V. Mirkhani, J. Mol. Catal. A: Chem. 385 (2014) 78‎‒‎‎84.
  6. M. Bahadori, S. Tangestaninejad, M. Moghadam, V. Mirkhani, A. Mechler, I. Mohammadpoor‎‒‎‎Baltork, F. Zadehahmadi, Micropor. Mesopor. Mater. 253 (2017) 102‎‒‎‎111.
  7. T. Begum, M. Mondal, M. P. Borpuzari, R. Kar, G. Kalita, P. K. Gogoi; U. Bora, Dalton Trans. 46 (2017) 539‎‒‎‎546.
  8. R. Fareghi‎‒‎‎Alamdari, M. S. Saeedi, F. Panahi, Appl. Organomet. Chem. (2017) e‎‒‎‎3870.
  9. D. A. Tomalia, J. M. J. Frechet, J. Polym. Sci., Part A: Polym. Chem., 9 (2002) 2719–2728.
  10. D. Astruc, E. Boisselier, C. Ornelas, Chem. Rev., 110 (2010) 1857–1959.
  11. G. R. Krishnan, K. Sreekumar, Polymer 49 (2008) 5233–5240.
  12. J. M. J. Frechet, D. A. Tomalia, in Dendrimers and other dendritic polymers, ed. Wiley, Amsterdam, The Netherlands (2001).
  13. B. Huang, D. A. Tomalia, J. Lumin. 111 (2005) 215–223.
  14. B. Huang, D. A. Tomalia, Inorg. Chim. Acta 359 (2006) 1961–1966.
  15. V. Chechik, R. M. Crooks, Langmuir 15 (1999) 6364–6369.
  16. D. Astruc, F. Lu, J. R. Aranzaes. Angew, Chem. 177 (2005) 8062‒8083; Angew. Chem. Int. Ed. 44 (2005) 7852–7872.
  17. M. B. Meder, I. Haller, L. H. Gade, Dalton Trans. (2005) 1403‒1415.
  18. G. D. Engel, L. H. Gade. Chem. Eur. J. 8 (2002) 4319‒4329.
  19. J. N. H. Reek, S. Arevalo, R. Van Heerbeek, P. C. J. Kamer, P. W. N. M. Van Leeuwen, Adv. Catal. 49 (2006) 71‒151.
  20. G. Jayamurugan, N. Jayaraman, Adv. Synth. Catal. 351 (2009) 2379‒2390.
  21. S. Lebreton, S. Monaghan, M. Bradley, Aldrichim. Acta 34 (2001) 75‒83.
  22. V. Swali, N. J. Wells, G. J. Langley, M. J. Bradley, Org. Chem. 62 (1997) 4902‒4903.
  23. A. Landarani Isfahani, I. Mohammadpoor‎–‎‏Baltork, V. Mirkhani, A. R. Khosropour, M. Moghadam, S. Tangestaninejad, R. Kia, Adv. Synth. Catal. 355 (2013) 957–972.
  24. A. Landarani Isfahani, I. Mohammadpoor‎–‎‏Baltork, V. Mirkhani, A. R. Khosropour, M. Moghadam, S. Tangestaninejad, Eur. J. Org. Chem. 2014 (2014) 5603–5609.
  25. A. Landarani Isfahani, I. Mohammadpoor‎–‎‏Baltork, V. Mirkhani, M. Moghadam, A. R. Khosropour, S. Tangestaninejad, M. Nasr‎–‎‏Esfahani, H. Amiri Rudbari, Synlett 25 (2014) 645−652.
  26. I. Mohammadpoor‎–‎‏Baltork, M. Moghadam, M. Nasr‎–‎‏Esfahani, A. R. Khosropour, S. Tangestaninejad, V. Mirkhani, A. Agabekov, H. Amiri Rudbari, RSC Adv. 4 (2014) :14291−14296.
  27. M. Nasr‎–‎‏Esfahani, I. Mohammadpoor‎–‎‏Baltork, A. R. Khosropour, M. Moghadam, V. Mirkhani, S. Tangestaninejad, H. Amiri Rudbari, J. Org. Chem. 79 (2014) 1437–1443.
  28. A. Daneshvar, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor‎–‎‏Baltork, A. Khalili, Organometallics 35 (2016)1747−1755.
  29. B. Asadi, I. Mohammadpoor‎–‎‏Baltork, S. Tangestaninejad, M. Moghadam, V. Mirkhani, A. Landarani‎–‎‏Isfahani, New J. Chem. 40 (2016) 6171‎–61‎‏84.
  30. M. Zakeri, M. Moghadam, V. Mirkhani, S. Tangestaninejad, I. Mohammadpoor‎–‎‏Baltork, Z. Pahlevanneshan, RSC Adv. 6 (2016) 104608‎–1046‎‏19.
  31. M. Zakeri, M. Moghadam, V. Mirkhani, S. Tangestaninejad, I. Mohammadpoor‎–‎‏Baltork, Z. Pahlevanneshan, Appl. Organomet. Chem. 32 (2018) e3937.
  32. S. Haghshenas Kashani, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor‎‒‎‎Baltork, Catal Lett. 148 (2018) 1110.
  33. M. Khajehzadeh, M. Moghadam, J. Organomet. Chem. 836 (2019) 60.