Palladium(II)-allyl complexes containing chiral N-donor ferrocenyl ligands

Journal of Organometallic Chemistry

Volumn 692, Issue 20, 2007, Pages 4215-4226

  Platero Prats, Ana E ^a   Pérez, Sonia ^a   López, Concepción ^a   Solans, Xavier ^a   Font Bardía, Mercè ^a   van Leeuwen, Piet W N M ^b   van Strijdonck, Gino P F ^b   Freixa, Zoraida ^b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Allylic alkylation; Chiral palladium(II) compounds; Ferrocene derivatives; Palladium(II) allyl complexes

Indexed keywords

ISOMERS; NITROGEN; NUCLEAR MAGNETIC RESONANCE; PALLADIUM; REACTION KINETICS; STOICHIOMETRY;

ALLYLIC ALKYLATION; COMPLEXES CONTAINING; FERROCENE DERIVATIVES; FERROCENYLIMINES; NUCLEOPHILE DIETHYL 2-METHYLMALONATE;

LIGANDS;

ACIS;

EID: 34548183084     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2007.06.016     Document Type: Article

References (61)

1. In: Togni A., and Hayashi T. (Eds). Ferrocenes. Homogeneous Catalysis. Organic Synthesis and Material Science (1995), VCH, Weinheim, Germany
2. In: Epstein J.A., Miller J.S., Gattesci D., Kahn O., Miller J.S., and Palacio F. (Eds). Molecular Materials NATO. ASI Series No. 198 (1990), Kluwer, Dordrecht, The Netherlands 151
3. Medina J.C., Gay I., Chen Z., Echegoyen L., and Gokel G.W. J. Am. Chem. Soc. 113 (1991) 365
4. Beer P.D., and Bernhardt P.V. J. Chem. Soc., Dalton Trans. (2001) 1428
5. Miyaji H., Collinson S.R., Prokeŝ I., and Tucker J.H.R. Chem. Commun. (2003) 64
6. For a general overview of additional and recent applications of this sort of compounds see for instance:. Otón F., Tárraga A., Espinosa A., Velasco M.D., and Molina P. Dalton Trans. (2006) 3685
7. Otón F., Tárraga A., Espinosa A., Velasco M.D., and Molina P. J. Org. Chem. 71 (2006) 4590
8. Cabrera S., Garci{dotless}́a-Mancheño O., Gómez Arrayás R., Alonso I., Mauleón P., and Carretero J.C. Pure Appl. Chem. 78 (2006) 257 and references therein
9. Moyano A., Rosol M., Moreno R.M., López C., and Maestro M.A. Angew. Chem., Int. Ed. 44 (2005) 1865
10. Kilroy T.G., Hennessy A.J., Connolly D.J., Malone Y.M., Farell A., and Guiry P.J. J. Mol. Catal. (A) 196 (2003) 65
11. Llobet A., Masllorens E., Moreno-Mañas M., Pla-Quintana A., Rodri{dotless}́guez M., and Roglans A. Tetrahedron Lett. 43 (2002) 1425
12. Vilaplana M.J., Molina P., Arques A., Andres C., and Pedrosa R. Tetrahedron: Asymmetry 13 (2002) 5
13. Bertogg A., Camponovo F., and Togni A. Eur. J. Inorg. Chem. (2005) 347
14. Coleman K.S., Turberville S., Pascu S.I., and Green M.L.H. J. Organomet. Chem. 690 (2005) 653
15. For recent applications of palladium(II) complexes containing bidentate ferrocenyl ligands see for instance:. Lam F.L., Au-Yeung T.T.L., Cheung H.Y., Kok S.H.L., Lam W.S., Wong K.Y., and Chan A.S.C. Tetrahedron: Asymmetry 17 (2006) 497
16. Cabrera S., Gómez Arrayas R., Alonso I., and Carretero J.C. J. Am. Chem. Soc. 127 (2005) 17938
17. Gibson V.C., Halliwell C.M., Long N.J., Oxford P.J., Smith A.M., White A.J.P., and Williams D.J. Dalton Trans. (2003) 918
18. Kmentova I., Battsengel B., Solcaniova E., and Toma S. Green Chem. 4 (2002) 103
19. Wildhalm M., Nettekoven U., Kalchhauser H., Mereiter K., Calhorda M.J., and Felix V. Organometallics 21 (2002) 315
20. Enders D., Peters R., Lochtman R., Raabe G., and Bats J.W. Eur. J. Org. Chem. (2000) 3399
21. Garci{dotless}́a Mancheño O., Priego J., Cabrera S., Gómez Arrayás R., Llamas T., and Carretero J.C. J. Org. Chem. 68 (2003) 3679
22. Deng W.P., You S.L., Huo X.L., Dai L.X., Yu Y.H., Xia W., and Sun J. J. Am. Chem. Soc. 123 (2001) 6508
23. You S.L., Hou X.L., Dai L.X., Yu Y.H., and Xia W. J. Org. Chem. 67 (2002) 4684
24. Barbaro P., Bianchini C., Giambastiani G., and Togni A. Tetrahedron Lett. 44 (2003) 8279
25. Gómez Arrayás R., Alonso I., Familiar O., and Carretero J.C. Organometallics 23 (2004) 1991
26. Anderson C.E., Donde Y., Douglas C.J., and Overman L.E. J. Org. Chem. 70 (2005) 648
27. Moreno R.M., Bueno A., and Moyano A. J. Organomet. Chem. 660 (2002) 62
28. Ojima I. Catalysis Asymmetric Synthesis. second ed. (2000), Wiley-VCH, New York, USA
29. Trost B.M., and Crawley M.L. Chem. Rev. 103 (2003) 2921
30. Helmchen G., Ernst M., and Paradies G. Pure Appl. Chem. 76 (2004) 495
31. Trost B.M. J. Org. Chem. 69 (2004) 5813
32. López C., Sales J., Solans X., and Zquiak R. J. Chem. Soc., Dalton Trans. (1992) 2321
33. Bosque R., López C., Sales J., Solans X., and Font-Bardía M. J. Chem. Soc., Dalton Trans. (1994) 735
34. López C., Bosque R., Solans X., and Font-Bardía M. New J. Chem. 20 (1996) 1285
35. Riera X., López C., Caubet A., Moreno V., Solans X., and Font-Bardía M. Eur. J. Inorg. Chem. (2001) 2135
36. López C., Caubet A., Pérez S., Solans X., and Font-Bardía M. Chem. Commun. (2004) 540
37. Benito M., López C., Solans X., and Font-Bardía M. Tetrahedron: Asymmetry 9 (1998) 4219
38. Cativiela C., Falvello L.R., Ginés J.C., Navarro R., and Urriolabeitia E.P. New J. Chem. 25 (2001) 344
39. López C., Caubet A., Pérez S., Solans X., Font-Bardía M., and Molins E. Eur. J. Inorg. Chem. (2006) 3974
40. Hansch C., Leo A., and Koeman D. Exploring QSAR Hydrophobic Electronic and Steric Constants (1995), ACS Professional Reference Book, Washington, USA
41. Onoue H., and Moritani I. J. Organomet. Chem. 43 (1972) 431
42. Wu Y.L., Ding L., Wang H., Liu L.H., Yuan H.Z., and Mao X.A. J. Organomet. Chem. 535 (1997) 49
43. Crespo M., Solans X., and Font-Bardía M. Organometallics 14 (1995) 355
44. Allen T.H. Acta Crystallogr. B58 (2002) 380
45. Kepert D.L. In: Wilkinson G., Guillard R.D., and McCleverty J.A. (Eds). Comprehensive Coordination Chemistry. The Synthesis Reactions Properties and Applications of Coordination Compounds vol. 1 (1987), Pergamon Press, Oxford, UK 38
46. López C., Bosque R., Solans X., and Font-Bardía M. J. Organomet. Chem. 535 (1997) 99
47. Codina G., Caubet A., López C., Moreno V., and Molins E. Helv. Chim. Acta 82 (1999) 1025
48. Herrmann H., Pregosin P.S., and Salzmann R. Organometallics 14 (1995) 3311 and references therein
49. López C., Pérez S., Solans X., Font-Bardía M., Roig A., Molins E., van Leeuwen P.W.N.M., and van Strijdonck G.P.F. Organometallics 26 (2007) 571
50. Co T.T., Paek S.W., Shim S.C., Cho C.S., Kim T.-J., Choi D.W., Kang S.O., and Jeong J.H. Organometallics 22 (2003) 1475
51. Szafran Z., Pike P.E., and Singh M.M. Microscale Inorganic Chemistry. A Comprehensive Laboratory Experience (1991), John Wiley and Sons, New York, USA
52. Auburn P.R., Mackenzie P.B., and Bosnich B. J. Am. Chem. Soc. 107 (1985) 2033
53. van Matt P., Lloyd-Jones G.C., Minidis B.E., Pfaltz A., Macko L., Neuburger M., Zehnder M., Rüegger H., and Pregosin P.S. Helv. Chim. Acta 78 (1995) 265
54. Perrin D.D., and Armarego W.L.F. Purification of Laboratory Chemicals. forth ed. (1996), Butterworth Heinemann, Oxford, UK
55. For 1a, 5a and 6a the labelling of the atoms correspond to those presented in Scheme 2.
56. Selected data.
57. The numbering scheme is presented in Fig. 1.
58. Sheldrick G.M. Shelxs. A Computer Program for Determination of Crystal Structure (1997), University of Göttingen, Germany
59. Sheldrick G.M. shelx97 A Computer Program for Determination of Crystal Structure (1997), University of Göttingen, Germany
60. International Tables of X-ray Crystallography, vol. IV, Kynoch Press, 1974, pp. 99-100 and 149.
61. Flack H.D. Acta Crystallogr. A43 (1983) 876