Cyclopalladation of N-phenyl-4-ferrocenylmethylpyrazoles: Crystal structure of [Pd{κ2-C,N-C6H4-1-[(3,5-Me 2-C3N2)-CH2-(η5-C 5H4)Fe(η5-C5H5)] }Cl(PPh3)] · CH2Cl2

Journal of Organometallic Chemistry

Volumn 693, Issue 12, 2008, Pages 2119-2131

  González, Asensio ^a   López, Concepción ^a   Solans, Xavier ^a   Font Bardía, Mercè ^a   Molins, Elies ^b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

Alkyne insertios; Cyclopalladation; Ferrocene derivatives; Palladacycles

Indexed keywords

COMPLEXATION; CRYSTAL STRUCTURE; DERIVATIVES; LIGANDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ALKYNE INSERTIOS; CYCLOPALLADATION; FERROCENE DERIVATIVES; PALLADACYCLES;

PALLADIUM COMPOUNDS;

EID: 43849110614     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2008.02.033     Document Type: Article

References (91)

1. For a general overview on cyclopalladated compounds and their applications, see:. Omae I. Applications of Organometallic Compounds (1998), Wiley, Chichester, UK [Chapter 20, p. 423]
2. Klaus A.J. In: Peters A.E., and Freeman H.S. (Eds). Modern Colorants. Synthesis and Structure vol. 3 (1995), Blackie Academic, London, UK 1
3. Thompson N.J., Serrano J.L., Baena M.J., and Espinet P. Chem. Eur. J. 2 (1996) 214
4. Wild S.B. Coord. Chem. Rev. 166 (1997) 291
5. Spencer J., and Pfeffer M. Adv. Met. Org. Chem. 6 (1998) 103
6. Pfeffer M. Recl. Trav. Chim. Pays-Bas 109 (1990) 567
7. Ryabov A.D. Synthesis (1985) 233 and references cited therein
8. For applications of palladacycles in homogeneous catalysis, see:. Gruber A.S., Zim D., Ebeling G., and Monteiro A.L. Org. Lett. 2 (2000) 2187
9. Dupont J., Pfeffer M., and Spencer J. Eur. J. Inorg. Chem. (2001) 1917
10. Gai X., Grigg R., Ramzan M.I., Sridharan V., Collard S., and Muir J.E. Chem. Commun. (2000) 2053 and references cited therein
11. For examples of the antitumoral activity of cyclopalladated complexes:. Higgins J.D., Neely L., and Fricker S.J. J. Inorg. Biochem. 49 (1993) 149
12. Navarro-Ranninger C., López-Solera I., Pérez J.M., Masaguer J.R., and Alonso C. Appl. Organomet. Chem. 7 (1993) 57
13. Navarro-Ranninger C., López-Solera I., González V.M., Pérez J.M., Alvarez-Valdes A., Martin A., Raithby P.R., Masaguer J.R., and Alonso C. Inorg. Chem. 35 (1996) 5181
14. For macromolecules containing cyclopalladated units, see:. López-Torres M., Fernández A., Fernández J.J., Suárez A., Castro-Juiz S., Vila J.M., and Pereira M.T. Organometallics 20 (2001) 1350
15. López C., Caubet A., Pérez S., Solans X., and Font-Bardía M. J. Organomet. Chem. 681 (2003) 80
16. Fernández A., Pereira E., Fernández J.J., López-Torres M., Suarez A., Mosteiro R., Pereira M.T., and Vila J.M. New J. Chem. 26 (2002) 895
17. For recent examples of the use of palladacycles in organic and organometallic synthesis, see:. Solé D., Vallverdú L., Solans X., Font-Bardía M., and Bonjoch J. Organometallics 24 (2004) 1438
18. Solé D., Vallverdú L., Solans X., Font-Bardía M., and Bonjoch J. J. Am. Chem. Soc. 125 (2003) 1587
19. Gul N., Nelson J.H., Willis A.C., and Ross A.D. Organometallics 21 (2002) 2041
20. Pérez S., López C., Caubet A., Pawelczyk A., Solans X., and Font-Bardía M. Organometallics 22 (2003) 2396
21. For advances in the cyclopalladation process, see:. Omae I. J. Organomet. Chem. 692 (2007) 2608
22. Godula K., and Sames D. Science 312 (2006) 67
23. Dupont J., Consorti C.S., and Spencer J. Chem. Rev. 105 (2005) 2527
24. López C., Pérez S., Solans X., Font-Bardía M., Roig A., Molins E., van Leeuwen P.W.N.M., and vand Strijdonck G.P.F. Organometallics 26 (2007) 571
25. Zhang T.-K., Yuan K., and Hou X.-L. J. Organomet. Chem. 692 (2007) 1912
26. Evans P.G., Brown N.A., Clarkson G.J., Newman C.P., and Rourke J.P. J. Organomet. Chem. 691 (2006) 1251
27. Pérez S., López C., Caubet A., Solans X., Font-Bardía M., Roig A., and Molins E. Organometallics 25 (2006) 596
28. Moyano A., Rosol M., Moreno R.M., López C., and Maestro M.A. Angew. Chem., Int. Ed. 44 (2005) 1865
29. Weiss M.E., Fischer D.F., Xin Z., Jautze S., Schweizer W.B., and Peters R. Angew. Chem., Int. Ed. 45 (2006) 5694
30. Anderson C.E., Donde Y., Yariv D., Christopher J., and Overman L.E. J. Org. Chem. 70 (2005) 648
31. In: Togni A., and Hayashi T. (Eds). Ferrocenes. Homogeneous Catalysis, Organic Synthesis. Materials Science (1995), VCH, Weinheim (Germany)
32. Gómez Arrayas R., Adrio J., and Carretero J.C. Angew. Chem., Int. Ed. 45 (2006) 7674
33. van Staveren D.R., and Metzler-Nolte N. Chem. Rev. 104 (2004) 5931
34. Hollis T.K., and Overman L.E. J. Organomet. Chem. 576 (1999) 290
35. Donde Y., and Overman L.E. J. Am. Chem. Soc. 121 (1999) 2933
36. Gonzalez A., Granell J., and López C. J. Organomet. Chem. 637-639 (2001) 116
37. Alonso M.T., Juanes O., de Mendoza J., and Rodríguez-Ubis J.C. J. Organomet. Chem. 430 (1992) 335
38. Boev V.I., Snegur L.V., Babin V.N., and Nekresov Y.S. Russ. Chem. Rev. 66 (1997) 613
39. Pagel K., Werner A., and Friedrichsen W. J. Organomet. Chem. 481 (1994) 109
40. González A., Marquet J., and Moreno-Mañas M. Tetrahedron 42 (1986) 4253
41. Gmelin Handbuch der Anorganische Chemie. Eisen Organische Verbindungen. Ferrocen. Springer-Verlag, Heildelberg, (Germany) 1977-1986, part A1-A8.
42. López C., Bosque R., Solans X., and Font-Bardía M. New J. Chem. 20 (1996) 1285
43. Geiger W.E. Organometallics 26 (2007) 5738
44. Brown E.R., and Sandifer J.R. In: Rossiter B.W., and Hamilton J.H. (Eds). Physical Methods in Chemistry: Electrochemical Methods vol. 4 (1986), Wiley, New York, USA (Chapter 4)
45. Blom N.F., Neuse E.W., and Thomas H.G. Trans. Met. Chem. 12 (1987) 301
46. Zanello P., Cinquantini A., Mangani S., Opromolla G., Pardi L., Janiak C., and Rausch M.D. J. Organomet. Chem. 471 (1994) 171
47. Hoh G.L.K., McEwen W.E., and Kleinberg J. J. Am. Chem. Soc. 83 (1961) 3949
48. Bosque R., López C., and Sales J. Inorg. Chim. Acta 244 (1995) 141
49. Riera X., Caubet A., López C., and Moreno V. Inorg. Chim. Acta 18 (1999) 2549
50. Mochida T., Shimizu F., Shimizu H., Okazawa K., Sato F., and Kuwahara D. J. Organomet. Chem. 692 (2007) 1834
51. Mochida T., Shimizu H., Suzuki S., and Akasaka T. J. Organomet. Chem. 691 (2006) 4882
52. Zora M., Pinar A.N., Odabasoglu M., Büyükgüngör O., and Turgut G. J. Organomet. Chem. 693 (2008) 145
53. Nakamoto K. IR and Raman Spectra of Inorganic and Coordination Compounds. 5th ed. (1997), Wiley, NewYork, USA
54. Allen F.H. Acta Crystallogr., Sect. B B58 (2002) 380
55. Navarro-Ranninger C., Zamora F., López-Solera I., Monge A., and Masaguer J.R. J. Organomet. Chem. 506 (1996) 149
56. Albert J., D'Andrea L., Granell J., Tavera R., Font-Bardía M., and Solans X. J. Organomet. Chem. 692 (2007) 3070
57. Fernández A., Vázquez-García D., Fernandez J.J., Lopez-Torres M., Suarez A., and Vila J.M. J. Organomet. Chem. 690 (2005) 3669
58. Riera X., López C., Caubet A., Moreno V., and Solans X. Eur. J. Inorg. Chem. (2001) 2135
59. Riera X., Caubet A., López C., Moreno V., Freisinger E., Willermann M., and Lippert B. J. Organomet. Chem. 629 (2001) 97
60. Bosque R., López C., Sales J., and Solans X. Dalton Trans. (1994) 735
61. Fernández A., Vázquez-García D., Fernández J.J., López-Torres M., Suárez A., Castro-Juiz S., and Vila J.M. New J. Chem. 26 (2002) 398
62. Hansch C., Leo A., and Koekman D. Exploring QSAR. Hydrophobic, Electronic and Steric Constants (1995), American Chemical Society, Washingthon, DC, USA
63. Vicente J., Arcas A., Bautista D., and Jones P.G. Organometallics 16 (1997) 2127
64. Vicente J., Abad J.A., Frankland A.D., and Ramirez De Arellano M.C. Chem. Eur. J. 5 (1999) 3066
65. Vicente J., Abad J.A., Martínez-Viviente E., and Jones P.G. Organometallics 21 (2002) 4454
66. Bondi A. J. Phys. Chem. 64 (1964) 441
67. Kitaigorodskii A.I. Molecular Crystals and Molecules (1973), Academic Press, London, UK
68. Steiner T. Acta Crystallogr., Sect. B B54 (1998) 456
69. In: Wilkinson G., Stone F.G.A., and Abel E.W. (Eds). Comprehensive Organometallic Chemistry. The Synthesis, Reactions and Structure of Organometallic Compounds vol. 6 (1982), Pergamon Press, New York, USA 236
70. -3 M molar solutions of 2 in acetonitrile (HPLC-grade) showed that the initial powdered solid sample of 2 did not dissolved completely and the initial solid sample turn into a gummy material. Complete dissolution or destruction of this residue was not achieved after stirring the mixture for 24 h at 298 K.
71. López C., and Granell J. J. Organomet. Chem. 555 (1998) 211
72. Little W.F., Reilley C.N., Johnson J.D., and Saunders A.P. J. Am. Chem. Soc. 86 (1964) 1376
73. Benito A., Cano J., Martínez-Mañez R., Soto J., Tendero M.J.L., Payá J., and Sinn E. Inorg. Chim. Acta 210 (1993) 233
74. Louati A., Gross M., Duce L., and Matt D. J. Organomet. Chem. 438 (1992) 167
75. Bracci M., Ercolani E., Floris B., Bassetti M., Chiesi-Villa A., and Guastini C. Dalton Trans. (1990) 1357
76. López C., Bosque R., Solans X., Font-Bardía M., Silver J., and Fern G. Dalton Trans. (1995) 1839
77. Benito M., López C., Morvan X., Solans X., and Font-Bardía M. Dalton Trans. (2000) 4470
78. López C., Pérez S., Solans X., and Font-Bardía M. J. Organomet. Chem. 690 (2005) 228
79. Geary W.J. Coord. Chem. Rev. 7 (1971) 87
80. Tao W., Silverberg L.J., Rheingold A.L., and Heck R.F. Organometallics 8 (1989) 2550
81. Sutter J.P., Pfeffer M., de Cian A., and Fischer J. Organometallics 11 (1992) 386
82. Pfeffer M., Sutter J.P., De Cian A., and Fischer J. Inorg. Chim. Acta 220 (1994) 115
83. Albinati A., Pregosin P.S., and Ruedi R. Helv. Chim. Acta 67 (1985) 2029
84. Zhao G., Wang Q.G., and Mak T.C.W. J. Organomet. Chem. 574 (1999) 311
85. Zhao G., Wang Q.G., and Mak T.C.W. Tetrahedron: Asymm. (1998) 2253
86. Zhao G., Wang Q.G., and Mak T.C.W. Tetrahedron: Asymm. (1998) 1557
87. Perrin D.D., Amarego W.L.F., and Perrin D.L. Purification of Laboratory Chemicals. 3rd ed. (1988), Butterworth-Heinemann, Oxford, UK
88. For the free ligands labeling of the atoms refers to those shown in Schemes 1 and 2; while for the palladium(II) complexes the numbering sequence is presented in Scheme 2 (for 2-6) and 3 (for 7 and 8).
89. Sheldrick G.M. shelxs A program for automatic solution of crystal structure (1997), University of Goettingen, Germany
90. Sheldrick G.M. shelx97 A program for automatic solution of crystal structure (1997), University Goettingen, Germany
91. International Tables of X-Ray Crystallography, Ed. Kynoch Press, 1974 vol. IV, pp. 99-100 and 149, Birmingham, UK.