Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Palladium(II) p-Tolylamide and Reaction with CO2 to Generate a Carbamato Derivative

  • Received : 2010.10.18
  • Accepted : 2010.10.21
  • Published : 2010.12.20
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Abstract

Pd(II) p-tolylamide Pd(2,6-$(Ph_2PCH_2)_2C_6H_3$)(NH($C_6H_4Me$-p)) (1) was metathetically prepared by the reaction of Pd(2,6-$(Ph_2PCH_2)_2C_6H_3$)Cl with NaNH($C_6H_4Me$-p). Treatment of 1 with carbon dioxide affords the palladium(II) carbamate Pd(2,6-$(Ph_2PCH_2)_2C_6H_3$)(OC(O)NH($C_6H_4Me$-p)) (2), quantitatively. Complex 2 reacts with HX (X = Cl, OTf) to give Pd(2,6-$(Ph_2PCH_2)_2C_6H_3$)X, $NH_2$(p-Tol) and $CO_2$. Reaction of the palladium(II) carbamate with MeI produced Pd(2,6-$(Ph_2PCH_2)_2C_6H_3$)I along with generation of methyl N-tolylcarbamate MeOC(O)NH($C_6H_4Me$-p), exclusively.

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References

  1. Sakakura, T.; Choi, J. C.; Yasuda, H. Chem. Rev. 2007, 107,2365. https://doi.org/10.1021/cr068357u
  2. McGhee, W. D.; Riley, D. P.; Christ, M. E.; Christ, K. M. Organometallics 1993, 12, .1429 https://doi.org/10.1021/om00028a069
  3. Fournier, J.; Bruneau,C.; Dixneuf, P. H.; Lecolier, S. J. Org. Chem. 1991, 56, 4456. https://doi.org/10.1021/jo00014a024
  4. Aresta, M.; Quaranta, E. ChemTech 1997, 27, 32.
  5. Gabriele, B.;Salerno, G.; Mancuso, R.; Costa, M. J. Org. Chem. 2004, 69, 4741. https://doi.org/10.1021/jo0494634
  6. Aresta, M.; Dibenedetto, A. Dalton Trans. 2007, 28, 2975.
  7. Mahe, R.; Sasaki, Y.; Bruneau, C.; Dixneuf, P. H. J. Org. Chem. 1989, 54, 1518. https://doi.org/10.1021/jo00268a008
  8. McGhee, W. D.; Riley, D. P. Organometallics 1992, 11, 900. https://doi.org/10.1021/om00038a060
  9. Aresta, M.; Dibenedetto, A.; Quaranta, E. J.Chem. Soc. Dalton Trans. 1995, 3359.
  10. Walther, D.; Geßler, S.;Ritter, U.; Schmidt, A.; Hamza, K.; Görls, H.; Sieler, J. Chem. Ber.1995, 128, 281. https://doi.org/10.1002/cber.19951280312
  11. Sneeden, R. P. A. In Comprehensive Organometallic Chemistry; Vol. 8, Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: New York, 1982; chapter 50.4, p 225.
  12. Leitner, W. Coord. Chem. Rev. 1996, 153, 257. https://doi.org/10.1016/0010-8545(95)01226-5
  13. Pandey, K. K. Coord. Chem.Rev. 1995, 140, 37. https://doi.org/10.1016/0010-8545(94)01120-Z
  14. Yin, X.; Moss, J. R. Coord. Chem. Rev. 1999, 181, 27. https://doi.org/10.1016/S0010-8545(98)00171-4
  15. Ozawa, F.; Ito, T.; Yamamoto, A. Chem. Lett. 1979, 735.
  16. Anillo, A.; Dell'Amico, D. B.; Calderazzo, F.; Nardelli, M.; Pelizzi, G.; Rocchi, L. J. Chem. Soc., Dalton Trans. 1991, 2845.
  17. Abram, U.; Dell'Amico, D. B.; Calderazzo, F.; Marchetti, L.; Strähle, J. J. Chem. Soc., Dalton Trans. 1999, 4093.
  18. Belforte, A.; Dell'Amico, D. B.; Calderazzo, F. Chem. Ber. 1988, 121, 1891. https://doi.org/10.1002/cber.19881211104
  19. Srivastava, R. S.; Singh, G.; Nakano, M.; Osakada, K.; Ozawa, F.; Yamamoto, A. J. Organomet. Chem. 1993, 451, 221. https://doi.org/10.1016/0022-328X(93)83029-U
  20. Cowan, R. L.; Trogler, W. C. J. Am. Chem. Soc. 1989, 111, 4750. https://doi.org/10.1021/ja00195a031
  21. Park, S.; Rheingold, A. L.; Roundhill, D. M. Organometallics 1991, 10, 615. https://doi.org/10.1021/om00049a020
  22. Boncella, J. M.; Villanueva, L. A. J.Organomet. Chem. 1994, 465, 297. https://doi.org/10.1016/0022-328X(94)87069-1
  23. Boncella, J. M.; Eve, T. M.; Rickman, B.; Abboud, K. Polyhedron 1998, 17, 725. https://doi.org/10.1016/S0277-5387(97)00373-2
  24. Alessio, R.; Dell’Amico, D. B.; Calderazzo, F.; Englert, U.; Guarini, A.; Labella, L.; Strasser, P. Helv. Chim. Acta 1998, 81, 219. https://doi.org/10.1002/hlca.19980810204
  25. Alessio, R.; Dell'Amico, D. B.; Calderazzo, F.; Englert, U. Gazz. Chim. Ital. 1993, 123, 719.
  26. Seligson, A. L.; Cowan, R. L.; Trogler, W. C. Inorg. Chem. 1991, 30, 3371. https://doi.org/10.1021/ic00018a003
  27. Glueck, D. S.; Winslow, L. J.; Bergman, R. G. Organometallics 1991, 10, 1462. https://doi.org/10.1021/om00051a044
  28. Ruiz, J.; Martnez, M. T.; Florenciano, F.; Rodrguez, V.; Lopez, G.; Prez, J.; Chaloner, P. A.; Hitchcock, P. B. Inorg. Chem. 2003, 42, 3650.
  29. Mandal, S. K.; Ho, D. M.; Orchin, M. Organometallics 1993, 12, 1714. https://doi.org/10.1021/om00029a032
  30. Hevia, E.; Perez, J.; Riera, L.; Riera, V.; delRio, I.; Garcia-Granda, S.; Miguel, D. Chem. Eur. J. 2002, 8, 4510. https://doi.org/10.1002/1521-3765(20021004)8:19<4510::AID-CHEM4510>3.0.CO;2-L
  31. Ryu, S. Y.; Kim, H.; Kim, H. S.; Park, S. J. Organomet. Chem. 1999, 592, 194. https://doi.org/10.1016/S0022-328X(99)00511-2
  32. Ryu, S. Y.; Yang, W.; Kim, H. S.; Park, S. Bull. Korean Chem. Soc. 1997, 18, 1183.
  33. Seul, J. M.; Park, S. J. Chem. Soc. Dalton Trans. 2002, 1153.
  34. Verkade, J. G. Chem. Rev. 1972, 9, 1.
  35. Pregosin, P. S.; Kunz, R. Helv. Chim. Acta 1975, 58, 423. https://doi.org/10.1002/hlca.19750580211
  36. Verstuyft, A. W.; Nelson, J. H.; Cary, L. W. Inorg. Chem. 1976, 15, 732. https://doi.org/10.1021/ic50157a050
  37. Pregosin, P. S.; Kunz, R. W. 31P- and 13C-NMR of Transition Metal Phosphine Complexes; Springer: Berlin, 1979; p 65.
  38. Bacchi, A.; Dell’Amico, D. B.; Calderazzo, F.; Giurlani, U.; Pelizzi, G.; Rocchi, L. Gazz. Chim. Ital. 1992, 122, 429.
  39. Dell’Amico, D. B.; Calderazzo, F.; Labella, L.; Maichle-Mossmer, C.; Strahle, J. J. Chem. Soc., Chem. Commun. 1994, 1555.
  40. Abram, U.; Dell’Amico, D. B.; Calderazzo, F.; Kaskel, S.; Labella, L.; Marchetti, F.; Rovai, R.; Strahle, J. Chem. Commun. 1997, 1941.
  41. Dell’Amico, D. B.; Calderazzo, F.; Marchetti, F.; Perego, G. J. Chem. Soc., Dalton Trans. 1983, 483.
  42. Dell’Amico, D. B.; Calderazzo, F.; Giurlani, U.; Pelizzi, G. Chem. Ber. 1987, 120, 955. https://doi.org/10.1002/cber.19871200613
  43. Abis, L.; Dell’Amico, D. B.; Busetto, C.; Calderazzo, F.; Caminiti, R.; Ciofi, C.; Garbassi, F.; Masciarelli, G. J. Mater. Chem. 1998, 8, 751. https://doi.org/10.1039/a705333i
  44. Abis, L.; Dell'Amico, D. B.; Busetto, C.; Calderazzo, F.; Caminiti, R.; Garbassi, F.; Tomei, A. J. Mater. Chem. 1998, 8, 2855. https://doi.org/10.1039/a804456b
  45. Rimml, H.; Venanzi, L. M. J. Organomet. Chem. 1983, 259, C6. 11.

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