On the formation of Pd(II) complexes of Trost modular ligand involving N-H activation or P,O coordination in Pd-catalyzed allylic alkylations

Journal of Organometallic Chemistry

Volumn 692, Issue 7, 2007, Pages 1457-1464

  Amatore, Christian ^a   Jutand, Anny ^a   Mensah, Laure ^a   Ricard, Louis ^b  

^a ECOLE NORMALE SUPÉRIEURE   (France)

^b LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

Allylic acetate; Allylic palladium; Oxidative addition; Palladium; Trost ligand

Indexed keywords

CATALYSIS; CHEMICAL BONDS; COMPLEXATION; COORDINATION REACTIONS; IONIZATION; MOLECULAR STRUCTURE;

ALLYLIC ACETATE; ALLYLIC PALLADIUM; OXIDATIVE ADDITION; TROST LIGANDS;

PALLADIUM COMPOUNDS;

EID: 33846817137     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2006.11.039     Document Type: Article

References (52)

1. Trost B.M., and Murphy D.J. Organometallics 4 (1985) 1143
2. Auburn P.R., Mackenzie P.B., and Bosnich B. J. Am. Chem. Soc. 107 (1985) 2033
3. Hayashi T. Pure Appl. Chem. 60 (1988) 7
4. Consiglio G., and Waymouth R. Chem. Rev. 89 (1989) 257
5. Hayashi T., Yamamoto T., Ito Y., Nishioha E., Miura H., and Yanagi K. J. Am. Chem. Soc. 111 (1989) 6301
6. Godleski S.A. In: Tost B.M., Pflemming I., and Semmelhack M.F. (Eds). Compr. Org. Synth. Vol. 4 (1991), Pergamon, Oxford
7. Frost C.G., Howard J., and Williams J.M.J. Tetrahedron Asymmtr. 3 (1992) 1089
8. Sawamura M., and Ito Y. Chem. Rev. 92 (1992) 857
9. Pfaltz A. Acc. Chem. Rev. 26 (1993) 339
10. Barbaro P., Pregosin P.S., Salzman R., Albinati A., and Kunz R.W. Organometallics 14 (1995) 5160
11. Herrmann J., Pregosin P.S., Salzman R., and Albinati A. Organometallics 14 (1995) 3311
12. Tsuji J. Palladium Reagents and Catalysts (1996), Wiley, Chichester p. 290
13. Pregosin P.S., and Salzman R. Coord. Chem. Rev. 155 (1996) 36
14. Trost B.M. Acc. Chem. Res. 29 (1996) 355
15. Trost B.M., and Van Vranken D.L. Chem. Rev. 96 (1996) 395
16. Togni A., Burckhardt U., Gramlich V., Pregosin P.S., and Salzman R. J. Am. Chem. Soc. 118 (1996) 1031
17. Baltzer N., Macko L., Schaffner S., and Zehnder M. Helv. Chim. Acta. 79 (1996) 803
18. Burckhardt U., Gramlich V., Hofmann P., Nesper R., Pregosin P.S., Salzman R., and Togni A. Organometallics 15 (1996) 3496
19. Steinhagen H., Reggelin S., and Helmchen G. Angew. Chem. Int. Ed. Engl. 36 (1997) 2108
20. Pregosin P.S., and Salzman R. Organometallics 18 (1999) 1207
21. Helmchen G., and Pfaltz A. Acc. Chem. Res. 33 (2000) 336
22. Watson D.G., and Trost B.M. Chem. Rev. 103 (2003) 2921
23. Markert C., and Pfaltz A. Angew. Chem. Int. Ed. 43 (2004) 2498
24. Watson I.D.G., and Yudin A.K.J. J. Am. Chem. Soc. 127 (2005) 17516
25. Amatore C., Bahsoun A.A., Jutand A., Mensah L., Meyer G., and Ricard L. Organometallics 24 (2005) 1569
26. For the use of the ligand 4 in Pd-catalyzed reactions, see: (a) Ref [2m] and.
27. Trost B.M., and Bunt R.C. Angew. Chem. Int. Ed. 35 (1996) 99
28. Trost B.M., Bunt R.C., Lemoine R.C., and Calkins T.L. J. Am. Chem. Soc. 122 (2000) 5968
29. Dominguez B., Hodnett N.S., and Lloyd-Jones G.C. Angew. Chem. Int. Ed. 40 (2001) 4289
30. Takahashi Y., Ito Ts., and Ishii Y. J. Chem. Soc. Chem. Commun. (1970) 1065
31. Leung W., Cosway S., Jones R.H.V., McCann H., and Wills M. J. Chem. Soc. Perkins Trans. 1 (2001) 2288
32. Hayashi T., Yamamoto A., Ito Y., Nishioha E., Miura H., and Yanagi K. J. Am. Chem. Soc. 111 (1989) 6301
33. 0(dba)(P,P) complexes see:. Amatore C., Broeker G., Jutand A., and Khalil F. J. Am. Chem. Soc. 119 (1997) 5176
34. Amatore C., and Jutand A. Coord. Chem. Rev. 178-180 (1998) 511
35. L. Mensah, PhD thesis, University Pierre et Marie Curie VI, Paris, October 5, 2005.
36. Trost B.M., Breit B., and Organ M.G. Tetrahedron Lett. 35 (1994) 5187
37. Trost B.M., and Toste F.D. J. Am. Chem. Soc. 121 (1999) 4545
38. E. Filali, G.C. Lloyd-Jones, unpublished work.
39. G.C. Lloyd-Jones, personal communication, E-mail exchange on January 7, 2004.
40. 31P NMR spectra at 28.79 ppm. Complex 5 was formed when the NMR tube was prepared in an atmosbag filled with Argon.
41. For oxidative addition of amines with Pd(0) complexes, see:. Yamamoto T., Sano K., and Yamamoto A. Chem. Lett. (1982) 907
42. Siriwardana A.I., Kamada M., Nakamura I., and Yamamoto Y. J. Org. Chem. 70 (2005) 5932
43. For the displacement of a phosphine ligand by an amine, see:. Jutand A., Negri S., and Principaud A. Eur. J. Inorg. Chem. (2005) 631
44. For the use of conductivity measurement for the elucidation of the mechanism of Pd-catalyzed reactions, see:. Jutand A. Eur. J. Inorg. Chem. (2003) 2017
45. -1 within 4 h 20 at 30 °C [3].
46. 2 complexes see ref [3].
47. Fairlamb I.J.S., and Lloyd-Jones G.C. Chem. Commun. (2000) 2447
48. Amatore C., Gamez S., and Jutand A. J. Organomet. Chem. 624 (2001) 217
49. Butts C.P., Crosby J., Lloyd-Jones G.C., and Stephen S.C. Chem. Commun. (1999) 1707
50. Lloyd-Jones G.C. Synlett (2001) 161
51. Aramendia M.A., Lafont F., Moreno-Mañas M., Pleixats R., and Roglans A. J. Org. Chem. 64 (1999) 3592
52. Moreno-Mañas M., Pleixats R., Spengler J., Cherin C., Estrine B., Bouquillon S., Hénin F., Pla-Quintina A., and Roglans A. Eur. J. Org. Chem. (2003) 274