Cyclometallated palladium diphosphane compounds derived from the chiral ligand (S)-PhCH(Me)NMe2. Michael addition reactions to the vinylidene double bond

European Journal of Inorganic Chemistry

Volumn , Issue 11, 2011, Pages 1824-1832

  Mosteiro, Roberto ^a   Fernández, Alberto ^a   Vázquez García, Digna ^a   Lõpez Torres, Margarita ^a   Rodríguez Castro, Antonio ^a   Gõmez Blanco, Nina ^a   Vila, José M ^b   Fernández, Jesãs J ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Chiral ligands; Michael addition; Palladacycles; Palladium; Phosphane ligands

Indexed keywords

ACETONE; ADDITION REACTIONS; CHEMICAL BONDS; ORGANOMETALLICS; PALLADIUM; PALLADIUM COMPOUNDS; SODIUM BICARBONATE; SODIUM CARBONATE; SODIUM CHLORIDE;

ADDITION PRODUCTS; CHIRAL LIGAND; DINUCLEAR; DIPHOSPHANE; DOUBLE BONDS; MICHAEL ADDITION REACTIONS; MICHAEL ADDITIONS; MOLAR RATIO; PALLADACYCLES; PHOSPHANE LIGANDS;

LIGANDS;

EID: 79953694781     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.201000873     Document Type: Article

References (79)

1. W. T. S. Huck, R. Hulst, P. Timmerman, F. C. J. M. van Veggel, D. N. Reinhoudt, Angew. Chem. Int. Ed. Engl. 1997, 36, 1006.
2. J. R. Hall, S. J. Loeb, G. K. H. Shimizu, G. P. A. Yap, Angew. Chem. Int. Ed. 1998, 37, 121.
3. W. T. S. Huck, L. J. Prins, R. H. Fokkers, N. M. M. Nibbering, F. C. J. M. van Veggel, D. N. Reinhoudt, J. Am. Chem. Soc. 1998, 120, 6240.
4. R. F. Carina, A. F. Williams, G. Bernardinelli, Inorg. Chem. 2001, 40, 1827.
5. M. Lõpez-Torres, A. Fernández, J. J. Fernández, A. Suárez, S. Castro-Juiz, J. M. Vila, M. T. Pereira, Organometallics 2001, 20, 1350.
6. M. Q. Slagt, D. A. P. van Zwieten, A. J. C. M. Moerkerk, R. J. M. Klein Gebbink, G. van Koten, Coord. Chem. Rev. 2004, 248, 2275.
7. W. Lu, V. A. L. Roy, C.-M. Che, Chem. Commun. 2006, 3972.
8. M. Gagliardo, G. Rodríguez, H. H. Dam, M. Lutz, A. L. Spek, R. W. A. Havenith, P. Coppo, L. De Cola, F. Hartl, G. P. M. van Klink, G. van Koten, Inorg. Chem. 2006, 45, 2143.
9. M. Marcos, in: Metallomesogens, Synthesis, Properties and Applications (Ed.:, J. L. Serrano), VCH, Weinheim, 1996.
10. D. Pucci, G. Barneiro, A. Bellusci, A. Crispini, M. Ghedini, J. Organomet. Chem. 2006, 691, 1138.
11. S.-W. Lai, T.-C. Cheung, M. C. W. Chan, K.-K. Cheung, S.-M. Peng, C.-M. Che, Inorg. Chem. 2000, 39, 255.
12. B. Ma, P. I. Djurovich, M. E. Thompson, Coord. Chem. Rev. 2005, 249, 1501.
13. M. Ghedini, I. Aiello, A. Crispini, A. Golemme, M. La Deda, D. Pucci, Coord. Chem. Rev. 2006, 250, 1373.
14. M. S. Lowry, S. Bernhard, Chem. Eur. J. 2006, 12, 7970.
15. L.-L. Wu, C.-H. Yang, I.-W. Sun, S.-Y. Chu, P.-C. Kao, H.-H. Huang, Organometallics 2007, 26, 2017.
16. S. C. F. Kui, I. H. T. Sham, C. C. C. Cheung, C.-W. Ma, B. Pan, N. Zhu, C. M. Che, W.-F. Fu, Chem. Eur. J. 2007, 13, 417.
17. A. Habtemariam, B. Watchman, B. S. Potter, R. Palmer, S. Parsons, A. Parkin, P. J. Sadler, J. Chem. Soc., Dalton Trans. 2001, 1306.
18. T. Okada, I. M. El-Mehasseb, M. Kodaka, T. Tomohiro, K. Okamoto, H. Okuno, J. Med. Chem. 2001, 44, 4661.
19. A. Gõmez-Quiroga, C. Navarro-Ranninger, Coord. Chem. Rev. 2004, 248, 119.
20. J. Ruiz, J. Lorenzo, L. Sanglas, N. Cutillas, C. Vicente, M. D. Villa, F. X. Avilés, G. Lõpez, V. Moreno, J. Pérez, D. Bautista, Inorg. Chem. 2006, 45, 6347.
21. J. Dupont, M. Pfeffer, J. Spencer, Eur. J. Inorg. Chem. 2001, 1917.
22. M. E. van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759.
23. J. Dupont, C. S. Consorti, J. Spencer, Chem. Rev. 2005, 105, 2527.
24. D. Amoroso, A. Jabri, P. A. Yap, D. G. Gusev, E. N. dos Santos, D. E. Fogg, Organometallics 2004, 23, 4047-4054.
25. J. Vicente, I. Saura-Llamas, C. Alcaraz, P. G. Jones, D. Bautisda, Organometallics 2002, 21, 3587-3595.
26. P. H. Leung, K. H. Ng, Y. Li, A. J. P. White, D. J. Williams, Chem. Commun. 1999, 2435.
27. S. B. Wild, Coord. Chem. Rev. 1997, 166, 291.
28. V. V. Dunina, O. N. Gorunova, M. V. Livantsov, Y. K. Grishin, Tetrahedron: Asymmetry 2000, 11, 2907.
29. F. Levrat, H. Stoeckli-Evans, N. Engel, Tetrahedron: Asymmetry 2002, 13, 2335.
30. J. Albert, J. Granell, G. Muller, D. Sainz, M. Font-Bardia, X. Solans, Tetrahedron: Asymmetry 1995, 6, 325.
31. V. V. Dunina, E. B. Golovan, N. S. Gulyukina, A. V. Buyevich, Tetrahedron: Asymmetry 1995, 6, 2731.
32. C. Lopez, R. Bosque, D. Sainz, X. Solans, M. Font-Bardia, Organometallics 1997, 16, 3261.
33. S. B. Wild, Coord. Chem. Rev. 1997, 166, 291.
34. J. Albert, R. Bosque, J. M. Cadena, J. R. Granell, G. Muller, J. I. Ordinas, Tetrahedron: Asymmetry 2000, 11, 3335.
35. J. Albert, J. M. Cadena, J. R. Granell, X. Solans, M. Font-Bardia, Tetrahedron: Asymmetry 2000, 11, 1943.
36. S. P. Flanagan, R. Goddard, P. J. Guiry, Tetrahedron 2005, 61, 9808.
37. L. Tang, Y. Zhang, L. Ding, Y. Li, K.-F. Mok, W.-C. Yeo, P.-H. Leung, Tetrahedron Lett. 2007, 48, 33.
38. T. Mino, Y. Tanaka, Y. Hattori, T. Yabusaki, H. Saotome, M. Sakamoto, T. Fujita, J. Org. Chem. 2006, 71, 7346-7353.
39. H. Brunner, A. Köllnberger, A. Mehmood, T. Tsuno, M. Zabel, J. Organomet. Chem. 2004, 689, 4244-4262.
40. F. Doro, M. Lutz, J. N. H. Reek, A. L. Spek, P. W. N. M. van Leeuwen, Eur. J. Inorg. Chem. 2008, 1309-1317.
41. P.-H. Leung, Acc. Chem. Res. 2004, 37, 169.
42. Y. Zhang, S. A. Pullarkat, Y. Li, P. Leung, Inorg. Chem. 2009, 48, 5535.
43. Y. Huang, S. A. Pullarkat, M. Yuan, Y. Ding, Y. Li, P. Leung, Organometallics 2010, 29, 536.
44. R. M. Stoop, A. Mezzetti, Organometallics 1998, 17, 668.
45. C. A. Tolman, Chem. Rev. 1977, 77, 313.
46. C. A. McAuliffe, W. Levason, Phosphane, Arsine and Stibine Complexes of the Transition Elements, Elsevier, Amsterdam, 1979.
47. D. W. Meek in Homogeneous Catalysis with Metal Phosphine Complexes (Ed.:, L. H. Pignolet), Plenum Press, New York, 1983.
48. B. Chaudret, B. Delavaux, R. Poilblanc, Coord. Chem. Rev. 1988, 86, 191.
49. O. Stelzer, K. P. Langhans in The Chemistry of Organophosphorus Compounds (Ed.:, F. R. Hartley), John Wiley & Sons, New York, 1990.
50. F. A. Cotton, B. Hong, Prog. Inorg. Chem. 1992, 40, 179.
51. J. L. Bookham, W. McFarlane, I. J. Colquhoun, J. Chem. Soc., Chem. Commun. 1986, 1041.
52. J. L. Bookham, W. McFarlane, Polyhedron 1988, 7, 129.
53. J. L. Bookham, W. McFarlane, M. Thornton-Pett, J. Chem. Soc., Dalton Trans. 1992, 2353.
54. H. Brunner, S. Limmer, J. Organomet. Chem. 1991, 413, 55.
55. A. M. Herring, S. H. Koskimies, B. L. Shaw, J. Organomet. Chem. 1988, 338, 13.
56. F. S. M. Hassan, B. L. Shaw, M. Thornton-Pett, J. Chem. Soc., Dalton Trans. 1988, 89.
57. P. A. Dolby, M. M. Harding, N. Nawar, A. K. Smith, J. Chem. Soc., Dalton Trans. 1992, 2939.
58. N. Nawar, A. K. Smith, J. Organomet. Chem. 1995, 493, 239.
59. J. V. Barkley, S. J. Higgins, M. K. McCart, T. J. Pounds, Inorg. Chem. 1997, 36, 6188.
60. F. S. M. Hassan, S. J. Higgins, G. B. Jacobsen, B. L. Shaw, M. Thornton-Pett, J. Chem. Soc., Dalton Trans. 1988, 3011.
61. S. J. Higgins, B. L. Shaw, J. Chem. Soc., Dalton Trans. 1989, 1527.
62. G. King, S. J. Higgins, A. Hopton, J. Chem. Soc., Dalton Trans. 1992, 3403.
63. E. J. Fernandez, M. C. Gimeno, P. G. Jones, A. Laguna, E. Olmos, Organometallics 1997, 16, 1130.
64. H. Schmidbaur, R. Herr, G. Muller, J. Riede, Organometallics 1985, 4, 1208.
65. B. Teijido, R. Mosteiro, A. Fernández, M. Lõpez-Torres, A. Sua′rez, J. M. Vila, J. J. Fernández, Organometallics 2002, 21, 1304.
66. R. Mosteiro, A. Fernández, M. Lõpez-Torres, D. Vázquez-García, A. Suárez, J. J. Fernández, J. M. Vila, New J. Chem. 2002, 26, 1425.
67. A. Fernández, D. Vázquez-García, J. J. Fernández, M. Lõpez-Torres, A. Suárez, S. Castro-Juiz, J. M. Vila, Eur. J. Inorg. Chem. 2002, 2389.
68. L. Pauling, The Nature of the Chemical Bond, 3rd ed., Cornell University Press, New York, 1960.
69. Î conformation:, H. Jendralla, C. H. Li, E. Paulus, Tetrahedron: Asymmetry 1994, 5, 1297.
70. λ conformation:, N. W. Alcock, D. I. Hulmes, J. M. Brown, J. Chem. Soc., Chem. Commun. 1995, 395.
71. K. Tani, L. D. Brown, J. Ahmed, J. A. Ibers, M. Yokota, A. Nakamura, S. Otsuka, J. Am. Chem. Soc. 1977, 99, 7876.
72. 13C NMR of transition metal phosphane complexes, in: NMR Basic Principles and Progress (Eds.:, P. Diehl, E. Fluck, R. Kosfeld), Springer, Berlin, 1979, vol. 16.
73. O. Kühl, Phosphorus-31 NMR spectroscopy, Springer, Berlin, 2008.
74. L. Tusek-Bozic, M. Curic, P. Traldi, Inorg. Chim. Acta 1997, 254, 49.
75. H. Schmidbaur, R. Herr, J. Riede, Chem. Ber. 1984, 117, 2322.
76. W. L. Steffen, G. J. Palenik, Inorg. Chem. 1976, 15, 2432.
77. C. L. Lee, Y. P. Yang, S. Rettig, B. R. James, D. A. Nelson, M. A. Lilga, Organometallics 1986, 5, 2220.
78. W. L. F. Armarego, D. D. Perrin, Purification of Laboratory Chemicals, 4th ed., Butterworth-Heinemann, Oxford, 1997.
79. For a short history of SHELX, see:, G. M. Sheldrick, Acta Crystallogr., Sect. A 2008, 64, 112.