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Vol. 26 No. 20 (2014)

Copyright (c) 2014 Muhammad Tariq Jan1, Shaukat Ali1, Shabir Ahmad1, Mohammed A.T. Abdel-Reheem2, Iqbal Hussain1, Riaz Ullah4

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This work is licensed under a Creative Commons Attribution 4.0 International License.

Hydroformylation of Styrene, Vinyl Acetate and Allyl Cyanide with Air-Stable Rhodium Catalysts Ligated by C2-Symmetric bis-N-Heterocyclic Carbenes

https://doi.org/10.14233/ajchem.2014.17386
Muhammad Tariq Jan1
1Department of Chemistry, Islamia College, Peshawar, Pakistan 2Research Center, College of Science, King Saud University, Riyadh, Saudi Arabia 3Biochemistry Department, Faculty of Agriculture, Ain Shams University, Cairo, Egypt 4Department of Chemistry, Government College, Ara Khel FR Kohat, KPK, Pakistan *Corresponding author: E-mail: afridiriaz@yahoo.com
Shaukat Ali1
1Department of Chemistry, Islamia College, Peshawar, Pakistan 2Research Center, College of Science, King Saud University, Riyadh, Saudi Arabia 3Biochemistry Department, Faculty of Agriculture, Ain Shams University, Cairo, Egypt 4Department of Chemistry, Government College, Ara Khel FR Kohat, KPK, Pakistan *Corresponding author: E-mail: afridiriaz@yahoo.com
Shabir Ahmad1
1Department of Chemistry, Islamia College, Peshawar, Pakistan 2Research Center, College of Science, King Saud University, Riyadh, Saudi Arabia 3Biochemistry Department, Faculty of Agriculture, Ain Shams University, Cairo, Egypt 4Department of Chemistry, Government College, Ara Khel FR Kohat, KPK, Pakistan *Corresponding author: E-mail: afridiriaz@yahoo.com
Mohammed A.T. Abdel-Reheem2
1Department of Chemistry, Islamia College, Peshawar, Pakistan 2Research Center, College of Science, King Saud University, Riyadh, Saudi Arabia 3Biochemistry Department, Faculty of Agriculture, Ain Shams University, Cairo, Egypt 4Department of Chemistry, Government College, Ara Khel FR Kohat, KPK, Pakistan *Corresponding author: E-mail: afridiriaz@yahoo.com
Iqbal Hussain1
1Department of Chemistry, Islamia College, Peshawar, Pakistan 2Research Center, College of Science, King Saud University, Riyadh, Saudi Arabia 3Biochemistry Department, Faculty of Agriculture, Ain Shams University, Cairo, Egypt 4Department of Chemistry, Government College, Ara Khel FR Kohat, KPK, Pakistan *Corresponding author: E-mail: afridiriaz@yahoo.com
Riaz Ullah4
1Department of Chemistry, Islamia College, Peshawar, Pakistan 2Research Center, College of Science, King Saud University, Riyadh, Saudi Arabia 3Biochemistry Department, Faculty of Agriculture, Ain Shams University, Cairo, Egypt 4Department of Chemistry, Government College, Ara Khel FR Kohat, KPK, Pakistan *Corresponding author: E-mail: afridiriaz@yahoo.com

Corresponding Author(s) : Muhammad Tariq Jan1

Asian Journal of Chemistry, Vol. 26 No. 20 (2014)

Abstract

This investigation describes an experimental examination of a new family of chiral rhodium complexes towards catalytic enantioselective hydroformylation. Both free bis-N-heterocyclic carbene and enetetramine ligand precursors are used to metallate Rh(I) salts under mild conditions. All catalysts prepared exhibit high conversion and regioselectivity for three substrates (styrene, vinyl acetate, allyl cycanide) but poor enantioselectivity.

Keywords

Hydroformylation Styrene Catalyst.
Tariq Jan1, M., Ali1, S., Ahmad1, S., A.T. Abdel-Reheem2, M., Hussain1, I., & Ullah4, R. (2014). Hydroformylation of Styrene, Vinyl Acetate and Allyl Cyanide with Air-Stable Rhodium Catalysts Ligated by C2-Symmetric bis-N-Heterocyclic Carbenes. Asian Journal of Chemistry, 26(20), 6911–6914. https://doi.org/10.14233/ajchem.2014.17386
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References
  1. C. Claver and P.W.N.M. van Leeuwen, In Rhodium Catalyzed Hydrofor-mylation; Kluwer Academic Publishers: Dordrecht, The Netherlands, Chap. 5 (2000).
  2. C. Claver, M. Dieguez, O. Pamies and S. Castillon, Top Organomet. Chem., 18, 35 (2006).
  3. F. Agbossou, J.-F. Carpentier and A. Mortreux, Chem. Rev., 95, 2485 (1995).
  4. Y. Yan and X. Zhang, J. Am. Chem. Soc., 128, 7198 (2006).
  5. B. Breit and W. Seiche, Synthesis, 1 (2001).
  6. B. Cornils, New Synthesis with Carbon Monoxide, Springer Verlag, Berlin (1980).
  7. C.D. Frohning and C.W. Kohlpainter, in eds.: B. Cornils and W.A. Herrmann, Applied Homogeneous Catalysis with Organometallic Compounds, VCH, Weinheim, Vol. 1, pp. 29-104 (1996).
  8. M. Tanaka, Y. Ikeda and I. Ogata, Chem. Lett., 1115 (1975).
  9. D. Evans, J.A. Osborn and G. Wilkinson, J. Chem. Soc. A, 3133 (1968).
  10. B. Cornils and W.A. Herrmann, Applied Homogeneous Catalysis, Wiley VCH, Weinheim (2002).
  11. R.L. Pruett and J.A. Smith, J. Org. Chem., 34, 327 (1969).
  12. T.P. Clark, C.R. Landis, S.L. Freed, J. Klosin and K.A. Abboud, J. Am. Chem. Soc., 127, 5040 (2005).
  13. A.T. Axtell, J. Klosin and K.A. Abboud, Organometallics, 25, 5003 (2006).
  14. J.R. Briggs and G.T. Whiteker, Chem. Commun., 2174 (2001).
  15. M. Bortenschlager, J. Schütz, D. von Preysing, O. Nuyken, W.A. Herrmann and R. Weberskirch, J. Org. Chem., 690, 6233 (2005).
  16. W.A. Herrmann, K. Öfele, D.V. Preysing and S.K. Schneider, J. Organomet. Chem., 687, 299 (2003).
  17. W.A. Herrmann, Angew. Chem. Int. Ed., 41, 1290 (2002).
  18. T. Weskamp, V.P.W. Böhm and W.A. Herrmann, J. Organomet. Chem., 600, 12 (2000).
  19. M. Regitz, Angew. Chem. Int. Ed. Engl., 35, 725 (1996).
  20. J. Huang, H.- Schanz, E.D. Stevens and S.P. Nolan, Organometallics, 18, 2370 (1999).
  21. E.D. Huang, E.D. Stevens, S.P. Nolan and J.L. Petersen, J. Am. Chem. Soc., 121, 2674 (1999).
  22. A.C. Hillier, W.J. Sommer, B.S. Yong, J.L. Petersen, L. Cavallo and S.P. Nolan, Organometallics, 22, 4322 (2003).
  23. T. Weskamp, F.J. Kohl, W. Hieringer, D. Gleich and W.A. Herrmann, Angew. Chem. Int. Ed., 38, 2416 (1999).
  24. E. Peris, J. Mata, J.A. Loch and R.H. Crabtree, Chem. Commun., 201 (2001).
  25. W.A. Herrmann, M. Elison, J. Fischer, C. Kocher and G.R. Artus, Angew. Chem. Int. Ed. Engl., 34, 2371 (1995).
  26. J.R. Miecznikowski and R.H. Crabtree, Organometallics, 23, 629 (2004).
  27. S. Gladiali, J.C. Bayon and C. Claver, Tetrahedron: Asymm., 6, 1453 (1995).
  28. C. Botteghi, S. Paganelli, A. Schionato and M. Marchetti, Chirality, 3, 355 (1991).
  29. J.-P. Rieu, A. Boucherle, H. Cousse and G. Mouzin, Tetrahedron, 42, 4095 (1986).
  30. M. Beller, B. Cornils, C.D. Frohning and C.W. Kohlpaintner, J. Mol. Catal., 104, 17 (1995).
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