C-and O-metallation of N-benzylideneamines by palladium (II). Synthesis and X-ray crystal structure of [Pd(2-{CH=N-(CH2)2-4′-(MeO)C6H4}-4,5-(MeO)2C6H2)Br(PPh3)]

Journal of Organometallic Chemistry

Volumn 522, Issue 1, 1996, Pages 59-67

  Albert, Joan ^a   Granell, Jaume ^a   Moragas, Rosa ^a   Font Bardía, Mercè ^a   Solans, Xavier ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

C metallation; Cyclometallation; Cyclopalladation; O metallation; Palladium; X ray structure

Indexed keywords

EID: 0030572555     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0022-328X(96)06182-7     Document Type: Article

References (51)

1. [1] (a) M.I. Bruce, Angew. Chem., Int. Ed. Engl., 16 (1977) 73;
2. (b) G.R. Newkome, W.E. Puckett, W.K. Gupta and G.E. Kiefer, Chem. Rev., 86 (1986) 451;
3. (c) I. Omae, Coord. Chem. Rev., 83 (1988) 137;
4. (d) V.V. Dunina, O.A. Zalevskaya and V.M. Potatov, Russ. Chem. Rev., 57 (1988) 250;
5. (e) A.D. Ryabov, Chem. Rev., 90 (1990) 403.
6. [2] (a) A.D. Ryabov, Synthesis, (1985) 233;
7. (b) M. Pfeffer, Recl. Trav. Chim. Pays Bas, 109 (1990) 567.
8. [3] P. Espinet, M.A. Esteruelas, L.A. Oro, J.L. Serrano and E. Sola, Coord. Chem. Rev., 117 (1992) 215.
9. [4] C. Navarro-Ranninger, I. López-Solera, J.M. Pérez, J.R. Masaguer and C. Alonso, Appl. Organomet. Chem., 7 (1993) 57.
10. [5] (a) S.Y.M. Chooi, P.H. Leung, C.C. Lim, K.F. Mok, G.H. Quek, K.Y. Sim and M.K. Tan, Tetrahedron: Asymm., 3 (1992) 529;
11. (b) E.P. Kyba and S.P. Rines, J. Org. Chem., 47 (1982) 4800;
12. (c) J. Albert, J. Granell, G. Muller, D. Sainz, M. Font-Bardia and X. Solans, Tetrahedron: Asymm., 6 (1995) 325.
13. [6] (a) N.W. Alcock, J.M. Brown and D.I. Hulmes, Tetrahedron: Asymm., 4 (1993) 743;
14. (b) N. Gabbitas, G. Salem, M. Stems and A.C. Willis, J. Chem. Soc., Dalton Trans., (1993) 3271;
15. (c) S.Y.M. Chooi, S.Y. Siah, P.H. Leung and K.F. Mok, Inorg. Chem., 32 (1993) 4812;
16. (d) S. Gladiali, A. Dore, D. Fabbri, O. De Lucchi and M. Manassero, Tetrahedron: Asymm., 5 (1994) 511;
17. (e) M. Pabel, A.C. Willis and S.B. Wild, Angew. Chem., Int. Ed. Engl., 33 (1994) 1835;
18. (f) C.E. Barclay, G. Deeble, R.J. Doyle, S.A. Elix, G. Salem, T.L. Jones, S.B. Wild and A.C. Wilis, J. Chem. Soc., Dalton Trans., (1995) 57.
19. [7] J. Albert, J. Granell, J. Sales, X. Solans and M. Font, Organometallics, 5 (1986) 2567.
20. [8] J. Albert, J. Barro and J. Granell, J. Organomet. Chem., 408 (1991) 115.
21. [9] M. Crespo, M. Martínez, J. Sales, X. Solans and M. Font-Bardia, Organometallics, 11 (1992) 1288.
22. [10] M. Crespo, M. Martínez and J. Sales, J. Chem. Soc., Chem. Commun., (1992) 822; M. Crespo, M. Martínez and J. Sales, Organometallics, 12 (1993) 4297.
23. [10] M. Crespo, M. Martínez and J. Sales, J. Chem. Soc., Chem. Commun., (1992) 822; M. Crespo, M. Martínez and J. Sales, Organometallics, 12 (1993) 4297.
24. [11] (a) J. Albert, R.M. Ceder, M. Gómez, J. Granell and J. Sales, Organometallics, 11 (1992) 1536;
25. (b) J.M. Vila, A. Suarez, M.T. Pereira, E. Gayoso and M. Gayoso, Polyhedron, 6 (1987) 1003;
26. (c) S.F. Dyke and S.N. Quessy, Transit. Met. Chem., 7 (1982) 233;
27. (d) J.M. Vila, M.T. Pereira, E. Gayoso and M. Gayoso, Transit. Met. Chem., 11 (1986) 342.
28. [12] J. Albert, J. Granell, R. Moragas, J. Sales, M. Font-Bardia and X. Solans, J. Organomet. Chem., 494 (1995) 95.
29. [13] C.E. Jones, B.L. Shaw and B.L. Turtle, J. Chem. Soc., Dalton Trans., (1974) 992.
30. [14] R.A. Berthon, S.B. Colbran and D.C. Craig, Polyhedron, 11 (1992) 243.
31. [15] H. Yang, M.A. Khan and K.M. Nicholas, Organometallics, 12 (1993) 3485.
32. [16] K. Nakamoto, Infrared and Roman Spectra of Inorganic and Coordination Compounds, Wiley, New York, 3rd edn., 1978, p. 232.
33. [17] H. Onoue and I. Moritani, J. Organomet. Chem., 43 (1972) 431.
34. [18] J. Albert, M. Gómez, J. Granell, J. Sales and X. Solans, Organometallics, 9 (1990) 1405.
35. [19] (a) G.B. Deacon and R.J. Phillips, Coord. Chem. Rev., 33 (1980) 227;
36. (b) G.B. Deacon, F. Huber and R.J. Phillips, Inorg. Chim. Acta, 104 (1985) 41.
37. [20] (a) A.J. Canty, N.J. Minchin, B.W. Skelton and A.H. White, J. Chem. Soc., Dalton Trans., (1986) 2205;
38. (b) A.J. Canty, N.J. Minchin, B.W. Skelton and A.H. White, J. Chem. Soc., Dalton Trans., (1987) 1477;
39. (c) D.H.R. Barton, J. Khamsi, N. Ozbalik and J. Reibenspies, Tetrahedron, 46 (1990) 3111;
40. (d) G. Ferguson, J.F. Gallagher, M. McGrath, J.P. Sheehan, T.R. Spalding and J.D. Kennedy, J. Chem. Soc., Dalton Trans., (1993) 27.
41. [21] (a) M.A. Cinellu, S. Gladiali, G. Minghetti, S. Stoccoro and F. Demartin, J. Organomet. Chem., 401 (1991) 371;
42. (b) J. Vicente, J.A. Abad, J. Gil-Rubio, P.G. Jones and E. Bembenek, Organometallics, 12 (1993) 4151;
43. (c) J.M. Vila, M. Gayoso, A. Fernández, N.A. Bailey and H. Adams, J. Organomet. Chem., 448 (1993) 233.
44. [22] (a) G. Dyker, Angew. Chem., Int. Ed. Engl., 31 (1992) 1023;
45. (b) G. Dyker, J. Org. Chem., 58 (1993) 6426;
46. (c) G. Dyker, Chem. Ber., 127 (1994) 739.
47. [23] A.J. Atkins, A.J. Blake and M. Schröder, J. Chem. Soc., Chem. Commun., (1993) 353.
48. [24] S. Rüttimann, G. Bernardelli and A.F. Williams, Angew. Chem., Int. Ed. Engl., 32 (1993) 392.
49. [25] G.M. Sheldrick, Acta Crystallogr. Sect. A, A46 (1990) 467-473.
50. [26] G.M. Sheldrick, in preparation.
51. [27] International Tables of X-Ray Crystallography, Vol. IV, Kynoch Press, Birmingham, UK, 1974, pp. 99, 100, 149.