Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Chiral [Iminophosphoranyl]ferrocenes: Synthesis, Coordination Chemistry, and Catalytic Application

  • Co, Thanh Thien (Department of Applied Chemistry, Kyungpook National University) ;
  • Shim, Sang-Chul (Department of Applied Chemistry, Kyungpook National University) ;
  • Cho, Chan-Sik (Department of Applied Chemistry, Kyungpook National University) ;
  • Kim, Dong-Uk (Department of Science Education, Daegu National University of Education) ;
  • Kim, Tae-Jeong (Department of Applied Chemistry, Kyungpook National University)
  • Published : 2005.09.20
Download PDF
⟨ Previous Next ⟩

Abstract

A series of new chiral [iminophosphoranyl]ferrocenes, {${\eta}^5-C_5H_4-(PPh_2=N-2,6-R_2-C_6H_3)$}Fe{${\eta}^5-C_5H_3-1-PPh^2-2-CH(Me)NMe_2$} (1: R = Me, $^iPr$), {${\eta}^5{-C_5H_4-(PPh_2=N-2,6-R_2}^1-C_6H_3)$}Fe{${\eta}^5-C_5H_3-1-(PPh_2=N-2,6-R_2-C_6H_3)-2-CH(Me)R_2$} (2: $R^1\;=\;Me,\;^iPr;\;R^2\;=\;NMe_2$, OMe), and $({\eta}^5-C_5H_5)Fe${${\eta}^5-C_5H_4-1-PR_2-2-CH(Me)N=PPh_3$} (3:R = Ph, $C_6H_{11}$) have been prepared from the reaction of [1,1'-diphenylphosphino-2-(N,N-dimethylamino) ethyl]ferrocene with arylazides (1 & 2) and the reaction of phosphine dichlorides ($R_3PCl_{2}$) with [1,1'-diphenylphosphino-2-aminoethyl]ferrocene (3), respectively. They form palladium complexes of the type $[Pd(C_3H_5)(L)]BF_4$ (4-6: L = 1-3), where the ligand (L) adopts an ${\eta}^2-N,N\;(2)\;or\;{\eta}^2$-P,N (3) as expected. In the case of 1, a potential terdentate, an ${\eta}^2$-P,N mode is realized with the exclusion of the –=NAr group from the coordination sphere. Complexes 4-6 were employed as catalysts for allylic alkylation of 1,3-diphenylallyl acetate leading to an almost stoichiometric product yield with modest enantiomeric excess (up to 74% ee). Rh(I)-complexes incorporating 1-3 were also prepared in situ for allylic alkylation of cinnamyl acetate as a probe for both regio- and enantioselectivities of the reaction. The reaction exhibited high regiocontrol in favor of a linear achiral isomer regardless of the ligand employed.

Keywords

References

  1. Staudinger, H.; Meyer, J. J. Helv. Chim. Acta 1919, 2, 635 https://doi.org/10.1002/hlca.19190020164
  2. Johnson, A. V. Ylides and Imines of Phosphorus; Wiley: New York, 1993
  3. Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353 https://doi.org/10.1016/S0040-4020(01)92229-X
  4. The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley and Sons: Baffins Lane, England, 1994; Vol. 3
  5. In Inorganic and Organic Polymers II. Advanced Materials and Intermediates; Wisian-Neilson, P., Allcock, H. R., Wynne, K. J., Eds.; ACS Symposium Series 572; American Chemical Society: Washington, DC, 1994; Neilson, R. H., Jinkerson, D. L., Kucera, W. R., Longlet, J. J., Samuel, R. C., Wood, C. E., Chapter 18
  6. In Inorganic and Organic Polymers II. Advanced Materials and Intermediates; Wisian-Neilson, P., Allcock, H. R., Wynne, K. J., Eds.; ACS Symposium Series 572; American Chemical Society: Washington, DC, 1994; White, M. L., Matyjaszewski, K., Chapter 24
  7. Allcock, H. R. Science 1992, 255, 1106 https://doi.org/10.1126/science.255.5048.1106
  8. Manners, I. Angew. Chem., Int. Ed. Engl. 1996, 35, 1602 https://doi.org/10.1002/anie.199616021
  9. Dehnicke, K.; Krieger, M.; Massa, W. Coord. Chem. Rev. 1999, 182, 19 https://doi.org/10.1016/S0010-8545(98)00191-X
  10. Roesky, H. W.; Witt, M. Chem. Rev. 1994, 94, 1163 https://doi.org/10.1021/cr00029a001
  11. Spencer, L. P.; Altwer, R.; Wei, P.; Gelmini, L.; Gauld, J.; Stephan, D. W. Organometallics 2003, 22, 3841 and references therein https://doi.org/10.1021/om020954t
  12. Stephan, D. W.; Stewart, J. C.; Guerin, F.; Courtenay, S.; Kickham, J.; Hollink, E.; Beddie, C.; Hoskin, A.; Graham, T.; Wei, P.; Spence, R. E. v. H.; Xu, W.; Koch, L.; Gao, X.; Harrison, D. G. Organometallics 2003, 22, 1937 https://doi.org/10.1021/om020954t
  13. Sauthier, M.; Leca, F.; de Souza, R. F.; Bernardo-Gusmao, K.; Queiroz, L. F. T.; Toupet, L.; Reau, R. New. J. Chem. 2002, 26, 630
  14. Al-Benna, S.; Sarsfield, M. J.; Thornton-Pett, M.; Ormsby, D. L.; Maddox, P. J.; Bres, P.; Bochmann, M. J. Chem. Soc., Dalton Trans. 2000, 4247
  15. Kubo, K.; Nakazawa, H.; Inagaki, H.; Miyoshi, K. Organometallics 2002, 21, 1942 https://doi.org/10.1021/om0110484
  16. Vicente, J.; Abad, J.-A.; Clemente, R.; Lopez-Serrano, J.; de Arellano, M. C. R.; Jones, P. G.; Bautista, D. Organometallics 2003, 22, 4248
  17. Leeson, M. A.; Nicholson, B. K.; Olsen, M. R. J. Organomet. Chem. 1999, 579, 243 https://doi.org/10.1016/S0022-328X(99)00007-8
  18. Avis, M. W.; van der Boom, M. E.; Elsevier, C. J.; Smeets, W. J.; Spek, A. L. J. Organomet. Chem. 1997, 527, 263 https://doi.org/10.1016/S0022-328X(96)06684-3
  19. Avis, M. W.; Goosen, M.; Elsevier, C. J.; Veldman, N.; Kooijman, H.; Spek, A. L. Inorg. Chim. Acta 1997, 264, 43 https://doi.org/10.1016/S0020-1693(97)05591-6
  20. Sauthier, M.; Fornies-Camer, J.; Toupet, L.; Reau, R. Organometallics 2000, 19, 553
  21. Reetz, M.; Bohres, E.; Goddard, R. Chem. Commun. 1998, 935
  22. Marquarding, D.; Gokel, G. W.; Hoffman, P.; Ugi, I. K. J. Am. Chem. Soc. 1970, 92, 5389 https://doi.org/10.1021/ja00721a017
  23. Gokel, G. W.; Ugi, I. K. J. Chem. Educ. Chem. 1972, 49, 294 https://doi.org/10.1021/ed049p294
  24. Hayashi, T.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1974, 4405
  25. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, N.; Hamada, Y.; Matsumoto, A.; Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138 https://doi.org/10.1246/bcsj.53.1138
  26. Colacot, T. J. Chem. Rev. 2003, 103, 3101 https://doi.org/10.1021/cr000427o
  27. Hayashi, T. Acc. Chem. Res. 2000, 33, 354 https://doi.org/10.1021/ar990080f
  28. Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414 https://doi.org/10.1002/1521-3773(20001215)39:24<4414::AID-ANIE4414>3.0.CO;2-C
  29. Fu, G. C. Acc. Chem. Res. 2000, 33, 412 https://doi.org/10.1021/ar990077w
  30. Richards, C. F.; Lock, A. J. Tetrahedron: Asymmetry 1998, 9, 2377 https://doi.org/10.1016/S0957-4166(98)00251-1
  31. Schwink, L.; Knochel, P. Chem. Eur. J. 1998, 4(5), 950 https://doi.org/10.1002/(SICI)1521-3765(19980515)4:5<950::AID-CHEM950>3.0.CO;2-B
  32. Togni, A. In Metallocenes; Togni, A., Halterman, R. L., Eds.; Wiley: New York, 1998; pp 685-721
  33. Kagan, H. B.; Riant, O. Adv. Asymmetric Synth. 1997, 2, 189-235 https://doi.org/10.1016/S1874-5148(97)80006-1
  34. Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, 1995; pp 105-142
  35. Kim, T.-J.; Shim, S. C.; Cho, C. S.; Thanh, T. C.; Kang, S. O.; Ko, J. J.; Han, W. S. Organometallics 2005, 24, 4824
  36. Co, T. T.; Paek, S. W.; Shim, S. C.; Cho, C. S.; Kim, T.-J.; Choi, D. W.; Kang, S. O.; Jeong, J. H. Organometallics 2003, 22, 1475
  37. Paek, S. H.; Shim, S. C.; Cho, C. S.; Kim, T.-J. Synlett 2003, 849
  38. Hwang, G.-H.; Ryu, E.-S.; Park, D.-K.; Shim, S. C.; Cho, C. S.; Kim, T.-J.; Jeong, J. H.; Cheong, M. Organometallics 2001, 20, 5784
  39. Song, J.-H.; Cho, D.-J.; Jeon, S.-J.; Kim, Y.-H.; Kim, T.-J. Inorg. Chem. 1999, 38, 893
  40. Cho, D.-J.; Jeon, S.-J.; Kim, H.-S.; Shim, S. C.; Cho, C. S.; Kim, T.-J. Tetrahedron: Asymmetry 1999, 10, 3833
  41. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161 https://doi.org/10.1021/cr9407577
  42. Corey, E. J.; Pikul, S. Org. Synth. 1992, 71, 22
  43. Cossio, F. P.; Ganboa, I.; Palomo, C. Tetrahedeon Lett. 1985, 26, 3041 https://doi.org/10.1016/S0040-4039(00)98613-1
  44. Cullen, W. R.; Einstein, F. W. B.; Huang, C.-H.; Willis, A. C.; Yeh, E.-S. J. Am. Chem. Soc. 1980, 102, 988
  45. Ball, R. G.; Payne, N. C. Inorg. Chem. 1977, 16, 1187 https://doi.org/10.1021/ic50171a042
  46. Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem. Int. Ed. 1995, 34, 462
  47. Trost, A. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104 https://doi.org/10.1021/ja973298a
  48. Glorius, F.; Pfaltz, A. Organic Lett. 1999, 1, 142
  49. Belda, O.; Kaiser, N.-F.; Bremberg, U.; Larhed, M.; Hallberg, A.; Moberg, C. J. Org. Chem. 2000, 65, 5868
  50. Glorius, F.; Neuburger, M.; Pfaltz, A. Helv. Chim. Acta 2001, 84, 3178 https://doi.org/10.1002/1522-2675(20011017)84:10<3178::AID-HLCA3178>3.0.CO;2-Q
  51. Trost, M.; Dogra, K.; Hayachi, I.; Emura, T.; Hughes, D. L.; Krska, S.; Reamer, R. A.; Palucki, M.; Yasuda, N.; Reider, P. J. Angew. Chem. Int. Ed. 2002, 41, 1929 https://doi.org/10.1002/1521-3773(20020603)41:11<1929::AID-ANIE1929>3.0.CO;2-O
  52. Evans, P. A.; Nelson, J. D. Tetrahedron Lett. 1998, 39, 1725 https://doi.org/10.1016/S0040-4039(98)00142-7
  53. Evans, P. A.; Kennedy, L. J. J. Am. Chem. Soc. 2001, 123, 1234 https://doi.org/10.1021/ja005689m
  54. Takeuchi, R.; Kashio, M. J. Am. Chem. Soc. 1998, 120, 8647 https://doi.org/10.1021/ja981560p
  55. Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol 4, pp 585-662
  56. Hayashi, T.; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561.; Pretot, R.; Pfaltz, A. Angew. Chem. Int. Ed. 1998, 37, 323 https://doi.org/10.1002/(SICI)1521-3773(19980216)37:3<323::AID-ANIE323>3.0.CO;2-T

Cited by

  1. The rhodium complex of bis(diphenylphosphinomethyl)dopamine-coated magnetic nanoparticles as an efficient and reusable catalyst for hydroformylation of olefins vol.39, pp.9, 2015, https://doi.org/10.1039/C5NJ01170A
  2. Chiral (iminophosphoranyl)ferrocenes: highly efficient ligands for rhodium- and iridium-catalyzed enantioselective hydrogenation of unfunctionalized olefins pp.33, 2006, https://doi.org/10.1039/b607450b
  3. Synthesis and structure of tetranuclear orthometallated Pd(ii) complexes derived from bis-iminophosphoranes pp.13, 2008, https://doi.org/10.1039/b718108f
  4. Chiral [Iminophosphoranyl]ferrocenes: Synthesis, Coordination Chemistry, and Catalytic Application. vol.37, pp.7, 2005, https://doi.org/10.1002/chin.200607031
  5. Imination reactions of free and coordinated 2-diphenylphosphino-1-phenyl-phospholane: Access to regioisomeric ruthenium(ii) complexes containing novel iminophosphorane-phosphine ligands vol.30, pp.9, 2005, https://doi.org/10.1039/b606781f
  6. Synthesis and reactivity studies of palladium(II) complexes containing the N-phosphorylated iminophosphorane-phosphine ligands Ph2PCH2P{&z.dbd;NP(&z.dbd;O)(OR) vol.2006, pp.47, 2006, https://doi.org/10.1039/b609359k
  7. Syntheses of Concave-Shaped [5,5,5]-Tricyclic Triquinanes by Pd-Catalyzed Enediyne Cycloreduction vol.28, pp.4, 2005, https://doi.org/10.5012/bkcs.2007.28.4.675
  8. Orthopalladation of iminophosphoranes: synthesis, structure and study of stability vol.2008, pp.9, 2008, https://doi.org/10.1039/b714485g
  9. Iminophosphoranylferrocenes as New Nucleophilic Organocatalysts for Regioselective Ring-opening of Epoxides vol.30, pp.12, 2005, https://doi.org/10.5012/bkcs.2009.30.12.3075