Synthesis and reactivity of new benzophenone imine derivatives containing the Ru(CO)(PiPr3)2 unit

Journal of Organometallic Chemistry

Volumn 526, Issue 1, 1996, Pages 73-83

  Bohanna, Cristina ^a   Esteruelas, Miguel A ^a   López, Ana M ^a   Oro, Luis A ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

Benzophenone imine; Orthometallation; Ruthenium hydride complexes

Indexed keywords

EID: 0030606213     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(96)06466-2     Document Type: Article

References (72)

1. [1] R. Nast, Coord. Chem. Rev., 47 (1982) 89.
2. [2] L.D. Field, A.V. George and T.W. Hambley, Inorg. Chem., 29 (1990) 4565.
3. [3] C. Bianchini, M. Peruzzini, F. Zanobini, P. Frediani and A. Albinati, J. Am. Chem. Soc., 113 (1991) 5453.
4. [4] Y. Wakatsuki, H. Yamazaki, N. Kumegawa, T. Satoh and J. Satoh, J. Am. Chem. Soc., 113 (1991) 9604.
5. [5] G. Jia, J.C. Galluci, A.L. Rheingold, B.S. Haggerty and D.W. Meek, Organometallics, 10 (1991) 3459.
6. [6] L.D. Field, A.V. George, E.Y. Malouf, I.H.M. Slip and T.W. Hambley, Organometallics, 10 (1991) 3842.
7. [7] A.K. McMullen, J.P. Selegue and J.G. Wang, Organometallics, 10 (1991) 3421.
8. [8] L.D. Field, A.V. George, G.R. Purches and I.H.M. Slip, Organometallics, 11 (1992) 3019.
9. [9] A. Santos, J. López, L. Matas, J. Ros, A. Galán and A.M. Echavarren, Organometallics, 12 (1993) 4215.
10. [10] M. Schäfer, N. Mahr, J. Wolf and H. Werner, Angew. Chem., Int. Ed. Engl., 32 (1993) 1315.
11. [11] R. Wiedermann, P. Steinert, M. Schäfer and H. Werner, J. Am. Chem. Soc., 115 (1993) 9864.
12. [12] C. Barbaro, C. Bianchini, M. Peruzzini, A. Polo, F. Zanobini and P. Frediani, Inorg. Chim. Acta, 220 (1994) 5.
13. [13] M. Schäfer, J. Wolf and H. Werner, J. Organomet. Chem., 485 (1995) 85.
14. [14] H. Werner, M. Schäfer, J. Wolf, K. Peters and H.G. von Schnering, Angew. Chem., Int. Ed. Engl., 34 (1995) 191.
15. [15] G. Albertin, S. Antoniutti, E. Bordingnon, F. Cazzaro, S. Ianelli and G. Pelizzi, Organometallics, 14 (1995) 4114.
16. [16] N. Hagihara, K. Sonogashira and S. Takahashi, Adv. Polym. Sci., 41 (1981) 149; K.J. Wynne and R. Rice, Annu. Rev. Mater. Sci., 14 (1984) 297; S. Takahashi, Y. Takai, H. Morimoto and K. Sonogashira, J. Chem. Soc., Chem. Commun., (1984) 3; S. Guha, C.C. Frazier, K. Kang and S.E. Finberg, Opt. Lett., 14 (1989) 952; W.J. Blau, H.J. Byrne, D.J. Cardin and A.P. Davey, J. Mater. Chem., 1 (1991) 245; Y. Sun, N.J. Taylor and A.J. Carty, Organometallics, 11 (1992) 4293; P. Espinet, M.A. Esteruelas, L.A. Oro, J.L. Serrano and E. Sola, Coord. Chem. Rev., 117 (1992) 215.
17. [16] N. Hagihara, K. Sonogashira and S. Takahashi, Adv. Polym. Sci., 41 (1981) 149; K.J. Wynne and R. Rice, Annu. Rev. Mater. Sci., 14 (1984) 297; S. Takahashi, Y. Takai, H. Morimoto and K. Sonogashira, J. Chem. Soc., Chem. Commun., (1984) 3; S. Guha, C.C. Frazier, K. Kang and S.E. Finberg, Opt. Lett., 14 (1989) 952; W.J. Blau, H.J. Byrne, D.J. Cardin and A.P. Davey, J. Mater. Chem., 1 (1991) 245; Y. Sun, N.J. Taylor and A.J. Carty, Organometallics, 11 (1992) 4293; P. Espinet, M.A. Esteruelas, L.A. Oro, J.L. Serrano and E. Sola, Coord. Chem. Rev., 117 (1992) 215.
18. [16] N. Hagihara, K. Sonogashira and S. Takahashi, Adv. Polym. Sci., 41 (1981) 149; K.J. Wynne and R. Rice, Annu. Rev. Mater. Sci., 14 (1984) 297; S. Takahashi, Y. Takai, H. Morimoto and K. Sonogashira, J. Chem. Soc., Chem. Commun., (1984) 3; S. Guha, C.C. Frazier, K. Kang and S.E. Finberg, Opt. Lett., 14 (1989) 952; W.J. Blau, H.J. Byrne, D.J. Cardin and A.P. Davey, J. Mater. Chem., 1 (1991) 245; Y. Sun, N.J. Taylor and A.J. Carty, Organometallics, 11 (1992) 4293; P. Espinet, M.A. Esteruelas, L.A. Oro, J.L. Serrano and E. Sola, Coord. Chem. Rev., 117 (1992) 215.
19. [16] N. Hagihara, K. Sonogashira and S. Takahashi, Adv. Polym. Sci., 41 (1981) 149; K.J. Wynne and R. Rice, Annu. Rev. Mater. Sci., 14 (1984) 297; S. Takahashi, Y. Takai, H. Morimoto and K. Sonogashira, J. Chem. Soc., Chem. Commun., (1984) 3; S. Guha, C.C. Frazier, K. Kang and S.E. Finberg, Opt. Lett., 14 (1989) 952; W.J. Blau, H.J. Byrne, D.J. Cardin and A.P. Davey, J. Mater. Chem., 1 (1991) 245; Y. Sun, N.J. Taylor and A.J. Carty, Organometallics, 11 (1992) 4293; P. Espinet, M.A. Esteruelas, L.A. Oro, J.L. Serrano and E. Sola, Coord. Chem. Rev., 117 (1992) 215.
20. [16] N. Hagihara, K. Sonogashira and S. Takahashi, Adv. Polym. Sci., 41 (1981) 149; K.J. Wynne and R. Rice, Annu. Rev. Mater. Sci., 14 (1984) 297; S. Takahashi, Y. Takai, H. Morimoto and K. Sonogashira, J. Chem. Soc., Chem. Commun., (1984) 3; S. Guha, C.C. Frazier, K. Kang and S.E. Finberg, Opt. Lett., 14 (1989) 952; W.J. Blau, H.J. Byrne, D.J. Cardin and A.P. Davey, J. Mater. Chem., 1 (1991) 245; Y. Sun, N.J. Taylor and A.J. Carty, Organometallics, 11 (1992) 4293; P. Espinet, M.A. Esteruelas, L.A. Oro, J.L. Serrano and E. Sola, Coord. Chem. Rev., 117 (1992) 215.
21. [16] N. Hagihara, K. Sonogashira and S. Takahashi, Adv. Polym. Sci., 41 (1981) 149; K.J. Wynne and R. Rice, Annu. Rev. Mater. Sci., 14 (1984) 297; S. Takahashi, Y. Takai, H. Morimoto and K. Sonogashira, J. Chem. Soc., Chem. Commun., (1984) 3; S. Guha, C.C. Frazier, K. Kang and S.E. Finberg, Opt. Lett., 14 (1989) 952; W.J. Blau, H.J. Byrne, D.J. Cardin and A.P. Davey, J. Mater. Chem., 1 (1991) 245; Y. Sun, N.J. Taylor and A.J. Carty, Organometallics, 11 (1992) 4293; P. Espinet, M.A. Esteruelas, L.A. Oro, J.L. Serrano and E. Sola, Coord. Chem. Rev., 117 (1992) 215.
22. [16] N. Hagihara, K. Sonogashira and S. Takahashi, Adv. Polym. Sci., 41 (1981) 149; K.J. Wynne and R. Rice, Annu. Rev. Mater. Sci., 14 (1984) 297; S. Takahashi, Y. Takai, H. Morimoto and K. Sonogashira, J. Chem. Soc., Chem. Commun., (1984) 3; S. Guha, C.C. Frazier, K. Kang and S.E. Finberg, Opt. Lett., 14 (1989) 952; W.J. Blau, H.J. Byrne, D.J. Cardin and A.P. Davey, J. Mater. Chem., 1 (1991) 245; Y. Sun, N.J. Taylor and A.J. Carty, Organometallics, 11 (1992) 4293; P. Espinet, M.A. Esteruelas, L.A. Oro, J.L. Serrano and E. Sola, Coord. Chem. Rev., 117 (1992) 215.
23. [17] C. Bohanna, M.A. Esteruelas, J. Herrero, A.M. López and L.A. Oro, J. Organomet. Chem., 498 (1995) 199.
24. [18] M.A. Esteruelas, M. Oliván, L.A. Oro and J.I. Tolosa, J. Organomet. Chem., 487 (1995) 143; M.A. Esteruelas, A.M. López, L.A. Oro and J.I. Tolosa, J. Mol. Catal. A: Chem., 96 (1995) 21; M.A. Esteruelas, M. Oliván and L.A. Oro, Organometallics, 15 (1996) 814.
25. [18] M.A. Esteruelas, M. Oliván, L.A. Oro and J.I. Tolosa, J. Organomet. Chem., 487 (1995) 143; M.A. Esteruelas, A.M. López, L.A. Oro and J.I. Tolosa, J. Mol. Catal. A: Chem., 96 (1995) 21; M.A. Esteruelas, M. Oliván and L.A. Oro, Organometallics, 15 (1996) 814.
26. [18] M.A. Esteruelas, M. Oliván, L.A. Oro and J.I. Tolosa, J. Organomet. Chem., 487 (1995) 143; M.A. Esteruelas, A.M. López, L.A. Oro and J.I. Tolosa, J. Mol. Catal. A: Chem., 96 (1995) 21; M.A. Esteruelas, M. Oliván and L.A. Oro, Organometallics, 15 (1996) 814.
27. [19] M.A. Esteruelas, F.J. Lahoz, M. Oliván, E. Oñate and L.A. Oro, Organometallics, 14 (1995) 3846.
28. [20] P.A. Chaloner, M.A. Esteruelas, F. Joó and L.A. Oro, Homogeneous Hydrogenation, Kluwer Academic, Boston, MA, 1994, Chap. 2 and 3.
29. [21] M.A. Esteruelas and H. Werner, J. Organomet. Chem., 303 (1986) 221.
30. [22] M.A. Esteruelas, E. Sola, L.A. Oro, H. Werner and U. Meyer, J. Mol. Catal., 45 (1988) 1; M.A. Esteruelas, E. Sola, L.A. Oro, H. Werner and U. Meyer, J. Mol. Catal., 53 (1989) 43.
31. [22] M.A. Esteruelas, E. Sola, L.A. Oro, H. Werner and U. Meyer, J. Mol. Catal., 45 (1988) 1; M.A. Esteruelas, E. Sola, L.A. Oro, H. Werner and U. Meyer, J. Mol. Catal., 53 (1989) 43.
32. [23] M.A. Esteruelas, J. Herrero and L.A. Oro, Organometallics, 12 (1993) 2377.
33. [24] H. Werner, U. Meyer, M.A. Esteruelas, E. Sola and L.A. Oro, J. Organomet. Chem., 366 (1989) 187.
34. [25] H. Werner, M.A. Esteruelas and H. Otto, Organometallics, 5 (1986) 2295.
35. [26] M.A. Esteruelas, F.J. Lahoz, A.M. López, E. Oñate and L.A. Oro, Organometallics, 13 (1994) 1669.
36. [27] M.A. Esteruelas, F.J. Lahoz, E. Oñate, L.A. Oro and B. Zeier, Organometallics, 13 (1994) 4258.
37. [28] C. Bohanna, M.A. Esteruelas, F.J. Lahoz, E. Oñate and L.A. Oro, Organometallics, 14 (1995) 4685.
38. [29] C. Bohanna, M.A. Esteruelas, F.J. Lahoz, E. Oñate, L.A. Oro and E. Sola, Organometallics, 14 (1995) 4825.
39. [30] M.L. Buil, M.A. Esteruelas, F.J. Lahoz, E. Oñate and L.A. Oro, J. Am. Chem. Soc., 117 (1995) 3619.
40. [31] H. Werner, M.A. Esteruelas, U. Meyer and B. Wrackmeyer, Chem. Ber., 120 (1987) 11.
41. [32] M.A. Esteruelas, M.P. García, A.M. López, L.A. Oro, N. Ruiz, C. Schlünken, C. Valero and H. Werner, Irutrg. Chem., 31 (1992) 5580.
42. [33] G.C. Martin and J.M. Boncella, Organometallics, 8 (1989) 2968.
43. [34] T. Daniel, M. Müller and H. Werner, Inorg. Chem., 30 (1991) 3118.
44. [35] H. Werner, T. Daniel, W. Knaup and O. Nürnberg, J. Organomet. Chem., 462 (1993) 309.
45. [36] T. Daniel and H. Werner, Z. Naturforsch., 4b (1992) 1707.
46. [37] M.A. Esteruelas, F.J. Lahoz, A.M. López, E. Oñate and L.A. Oro, Organometallics, 14 (1995) 2496.
47. [38] T. Daniel, W. Knaup, M. Dziallas and H. Werner, Chem. Ber., 726 (1993) 1981.
48. [39] H. Werner, T. Daniel, T. Braun and O. Nürnberg, J. Organomet. Chem., 480 (1994) 145.
49. [40] M.I. Bruce, Chem. Rev., 91 (1991) 197.
50. [41] J.J. Low and W.A. Goddard, III, J. Am. Chem. Soc., 108 (1986) 6115.
51. [42] S. Komiga, Y. Abe, A. Yamamoto and T. Yamamoto, Organometallics, 2 (1983) 1466.
52. [43] A. Gillie and J.K. Stille, J. Am. Chem. Soc., 102 (1980) 4933.
53. [44] P.S. Braterman, R.J. Cross and G.B. Young, J. Chem. Soc., Dalton Trans., (1976) 1310; P.S. Braterman, R.J. Cross and G.B. Young, J. Chem. Soc., Dalton Trans., (1977) 1892.
54. [44] P.S. Braterman, R.J. Cross and G.B. Young, J. Chem. Soc., Dalton Trans., (1976) 1310; P.S. Braterman, R.J. Cross and G.B. Young, J. Chem. Soc., Dalton Trans., (1977) 1892.
55. [45] J. Chatt and B.L. Shaw, J. Chem. Soc., (1959) 705.
56. [46] W. Beck and K. Sünkel, Chem. Rev., 88 (1988) 1405.
57. [47] H.H. Karsch, H.F. Klein and H. Schmidbaur, Chem. Ber., 110 (1977) 2200.
58. [48] H. Werner and J. Gotzig, Organometallics, 2 (1983) 547.
59. [49] G. Erker, W. Frömberg, C. Krüger and E. Raabe, J. Am. Chem. Soc., 110 (1988) 2400.
60. [50] J.T. Poulton, K. Folting, W.E. Streib and K.G. Caulton, Inorg. Chem., 31 (1992) 3190; J.T. Poulton, M.P. Sigalas, O. Eisenstein and K.G. Caulton, Inorg. Chem., 32 (1993) 5490; R.H. Heyn, J.C. Huffman and K.G. Caulton, New J. Chem., 17 (1993) 797; J.T. Poulton, M.P. Sigalas, K. Folting, W.E. Streib, O. Eisenstein and K.G. Caulton, Inorg. Chem., 33 (1994) 1476.
61. [50] J.T. Poulton, K. Folting, W.E. Streib and K.G. Caulton, Inorg. Chem., 31 (1992) 3190; J.T. Poulton, M.P. Sigalas, O. Eisenstein and K.G. Caulton, Inorg. Chem., 32 (1993) 5490; R.H. Heyn, J.C. Huffman and K.G. Caulton, New J. Chem., 17 (1993) 797; J.T. Poulton, M.P. Sigalas, K. Folting, W.E. Streib, O. Eisenstein and K.G. Caulton, Inorg. Chem., 33 (1994) 1476.
62. [50] J.T. Poulton, K. Folting, W.E. Streib and K.G. Caulton, Inorg. Chem., 31 (1992) 3190; J.T. Poulton, M.P. Sigalas, O. Eisenstein and K.G. Caulton, Inorg. Chem., 32 (1993) 5490; R.H. Heyn, J.C. Huffman and K.G. Caulton, New J. Chem., 17 (1993) 797; J.T. Poulton, M.P. Sigalas, K. Folting, W.E. Streib, O. Eisenstein and K.G. Caulton, Inorg. Chem., 33 (1994) 1476.
63. [50] J.T. Poulton, K. Folting, W.E. Streib and K.G. Caulton, Inorg. Chem., 31 (1992) 3190; J.T. Poulton, M.P. Sigalas, O. Eisenstein and K.G. Caulton, Inorg. Chem., 32 (1993) 5490; R.H. Heyn, J.C. Huffman and K.G. Caulton, New J. Chem., 17 (1993) 797; J.T. Poulton, M.P. Sigalas, K. Folting, W.E. Streib, O. Eisenstein and K.G. Caulton, Inorg. Chem., 33 (1994) 1476.
64. [51] L.H. Chan and E.G. Rochow, J. Organomet. Chem., 9 (1967) 231; K. Farmey, M. Kilner and C. Midealf, J. Chem. Soc. A, (1970) 2279; K. Kilner, Adv. Organomet. Chem., 10 (1972) 115.
65. [51] L.H. Chan and E.G. Rochow, J. Organomet. Chem., 9 (1967) 231; K. Farmey, M. Kilner and C. Midealf, J. Chem. Soc. A, (1970) 2279; K. Kilner, Adv. Organomet. Chem., 10 (1972) 115.
66. [51] L.H. Chan and E.G. Rochow, J. Organomet. Chem., 9 (1967) 231; K. Farmey, M. Kilner and C. Midealf, J. Chem. Soc. A, (1970) 2279; K. Kilner, Adv. Organomet. Chem., 10 (1972) 115.
67. [52] A.D. Ryabov, Chem. Rev., 90 (1990) 403.
68. [53] R.C. Mehrota, in G. Wilkinson, R.D. Gillard and J.A. McCleverty (eds.), Comprehensive Coordination Chemistry, Vol. 2, Pergamon Press, Oxford, 1987, p. 269; H. Elsbernd and J.K. Beattie, J. Chem. Soc. A, (1970) 2598; B.C. Lane, J.E. Lester and F. Basolo, J. Chem. Soc., Chem. Commun., (1971) 1618; S. Joss, P. Bigler and A. Ludi, Inorg. Chem., 24 (1985) 3487; W.D. Harman and H. Taube, Inorg. Chem., 27 (1988) 3261.
69. [53] R.C. Mehrota, in G. Wilkinson, R.D. Gillard and J.A. McCleverty (eds.), Comprehensive Coordination Chemistry, Vol. 2, Pergamon Press, Oxford, 1987, p. 269; H. Elsbernd and J.K. Beattie, J. Chem. Soc. A, (1970) 2598; B.C. Lane, J.E. Lester and F. Basolo, J. Chem. Soc., Chem. Commun., (1971) 1618; S. Joss, P. Bigler and A. Ludi, Inorg. Chem., 24 (1985) 3487; W.D. Harman and H. Taube, Inorg. Chem., 27 (1988) 3261.
70. [53] R.C. Mehrota, in G. Wilkinson, R.D. Gillard and J.A. McCleverty (eds.), Comprehensive Coordination Chemistry, Vol. 2, Pergamon Press, Oxford, 1987, p. 269; H. Elsbernd and J.K. Beattie, J. Chem. Soc. A, (1970) 2598; B.C. Lane, J.E. Lester and F. Basolo, J. Chem. Soc., Chem. Commun., (1971) 1618; S. Joss, P. Bigler and A. Ludi, Inorg. Chem., 24 (1985) 3487; W.D. Harman and H. Taube, Inorg. Chem., 27 (1988) 3261.
71. [53] R.C. Mehrota, in G. Wilkinson, R.D. Gillard and J.A. McCleverty (eds.), Comprehensive Coordination Chemistry, Vol. 2, Pergamon Press, Oxford, 1987, p. 269; H. Elsbernd and J.K. Beattie, J. Chem. Soc. A, (1970) 2598; B.C. Lane, J.E. Lester and F. Basolo, J. Chem. Soc., Chem. Commun., (1971) 1618; S. Joss, P. Bigler and A. Ludi, Inorg. Chem., 24 (1985) 3487; W.D. Harman and H. Taube, Inorg. Chem., 27 (1988) 3261.
72. [53] R.C. Mehrota, in G. Wilkinson, R.D. Gillard and J.A. McCleverty (eds.), Comprehensive Coordination Chemistry, Vol. 2, Pergamon Press, Oxford, 1987, p. 269; H. Elsbernd and J.K. Beattie, J. Chem. Soc. A, (1970) 2598; B.C. Lane, J.E. Lester and F. Basolo, J. Chem. Soc., Chem. Commun., (1971) 1618; S. Joss, P. Bigler and A. Ludi, Inorg. Chem., 24 (1985) 3487; W.D. Harman and H. Taube, Inorg. Chem., 27 (1988) 3261.