Use of a bulky phosphine of weak σ-donicity with palladium as a versatile and highly-active catalytic system: Allylation and arylation coupling reactions at 10-1-10-4 mol% catalyst loadings of ferrocenyl bis(difurylphosphine)/Pd

Tetrahedron

Volumn 61, Issue 41, 2005, Pages 9759-9766

  Hierso, Jean Cyrille ^a   Fihri, Aziz ^a   Amardeil, Régine ^a   Meunier, Philippe ^a   Doucet, Henri ^b   Santelli, Maurice ^b  

^a UNIVERSITÉ DE BOURGOGNE   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Allylic substitution; Catalysis; Cross coupling; Ferrocenylphosphine; Furyl; Ligand effect; Palladium

Indexed keywords

ACETIC ACID; BROMIDE; CARBON; FERROCENE DERIVATIVE; NITROGEN; PALLADIUM; PHOSPHINE;

ALLYLATION; AMINATION; ARTICLE; ARYLATION; CATALYSIS; CATALYST; HECK REACTION; PRIORITY JOURNAL; SONOGASHIRA REACTION; SUBSTITUTION REACTION; SUZUKI REACTION;

EID: 24344438930     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.06.065     Document Type: Article

References (61)

1. V. Farina Adv. Synth. Catal. 346 2004 1519 1521
2. I.J.S. Fairlamb Annu. Rep. Prog. Chem., Sect. B 100 2004 113 148
3. V. Farina Adv. Synth. Catal. 346 2004 1553 1582
4. J.-C. Hierso, A. Fihri, R. Amardeil, P. Meunier, H. Doucet, M. Santelli, and B. Donnadieu Organometallics 22 2003 4490 4499
5. J.-C. Hierso, A. Fihri, R. Amardeil, P. Meunier, H. Doucet, M. Santelli, and V.V. Ivanov Org. Lett. 6 2004 3473 3476
6. J.-C. Hierso, V.V. Ivanov, R. Amardeil, P. Richard, and P. Meunier Chem. Lett. 33 2004 1296 1297
7. J.-C. Hierso, A. Fihri, V.V. Ivanov, B. Hanquet, N. Pirio, B. Donnadieu, B. Rebiere, R. Amardeil, and P. Meunier J. Am. Chem. Soc. 126 2004 11077 11087
8. D.W. Old, J.P. Wolfe, and S.L. Buchwald J. Am. Chem. Soc. 120 1998 9722 9723
9. J.P. Wolfe, and S.L. Buchwald Angew. Chem., Int. Ed. 38 1999 2413 2416
10. S.D. Walker, T.E. Barder, J.R. Martinelli, and S.L. Buchwald Angew. Chem., Int. Ed. 43 2004 1871 1876
11. A.F. Littke, and G.C. Fu J. Org. Chem. 64 1999 10 11
12. A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. 37 1999 3387 3388
13. A.F. Littke, C. Dai, and G.C. Fu J. Am. Chem. Soc. 122 2000 4020 4028
14. A.F. Littke, and G.C. Fu J. Am. Chem. Soc. 123 2001 6989 7000
15. B.C. Hamann, and J.F. Hartwig J. Am. Chem. Soc. 120 1998 7369 7370
16. A. Zapf, A. Ehrentraut, and M. Beller Angew. Chem., Int. Ed. 39 2000 4153 4155
17. V. Farina, and B. Krishnan J. Am. Chem. Soc. 113 1991 9585 9595
18. J.P. Collman, L.S. Hegedus, J.R. Norton, and R.G. Finke Principles and Applications of Organotransition Metal Chemistry 1987 University Science B. Mill Valley
19. A.H. Roy, and J.F. Hartwig Organometallics 23 2004 1533 1541
20. E. Galardon, S. Ramdeehul, J.M. Brown, A. Cowley, K.K. Hii, and A. Jutand Angew. Chem., Int. Ed. 41 2002 1760 1763
21. M. Kranenburg, P.C.J. Kamer, and P.W.N.M. Van Leeuwen Eur. J. Inorg. Chem. 1998 155 157
22. A.H. Roy, and J.F. Hartwig J. Am. Chem. Soc. 123 2001 1232 1233
23. A. Zapf, and M. Beller Chem. Eur. J. 6 2000 1830 1833
24. B.C. Hamann, and J.F. Hartwig J. Am. Chem. Soc. 120 1998 3694 3703
25. A. Togni, and T. Hayashi Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science 1995 VCH Weinheim
26. A.R. Elsagir, F. Gassner, H. Gorls, and E. Dinjus J. Organomet. Chem. 597 2000 139 145
27. T.J. Kim, Y.H. Kim, H.S. Kim, S.C. Shim, Y.W. Kwak, J.S. Cha, H.S. Lee, J.K. Uhm, and S.I. Byun Bull. Korean Chem. Soc. 13 1992 588 592
28. N.G. Andersen, and B.A. Keay Chem. Rev. 101 2001 997 1030
29. A.L. Bandini, G. Banditelli, M.A. Cinellu, G. Sanna, G. Minghetti, F. Demartin, and M. Manassero Inorg. Chem. 28 1989 404 410
30. G. Bandoli, and A. Dolmella Coord. Chem. Rev. 209 2000 161 196
31. Optimized conditions can be found upon systematic efforts on variation of the tandem base/solvent, the ratio of ligand, or the use of additives, see Ref. 22.
32. M. Feuerstein, F. Berthiol, H. Doucet, and M. Santelli Org. Biomol. Chem. 1 2003 2235 2237
33. M. Johannsen, and K.A. Jorgensen Chem. Rev. 98 1998 1689 1708
34. B.M. Trost, and D.L. Van Vranken Chem. Rev. 96 1996 395 422
35. M. Feuerstein, D. Laurenti, H. Doucet, and M. Santelli Chem. Commun. 2001 43 44
36. M. Feuerstein, D. Laurenti, H. Doucet, and M. Santelli Tetrahedron Lett. 42 2001 2313 2315
37. M. Feuerstein, D. Laurenti, H. Doucet, and M. Santelli J. Mol. Catal. A: Chem. 182-183 2002 471 480 and references therein
38. J. Tsuji Palladium Reagents and Catalysis: Innovations in Organic Synthesis 1995 Wiley Chichester p 292: the author indicates the necessity of bases for alkylation of allyl acetates
39. Using primary amines monoallylation products and diallylation products are obtained.
40. D.A. Albisson, R.B. Bedford, P. Noelle Scully, and S.E. Lawrence Chem. Commun. 1998 2095 2096
41. D.A. Albisson, R.B. Bedford, and P.N. Scully Tetrahedron Lett. 39 1998 9793 9796
42. G.P.F. Van Strijdonck, M.D.K. Boele, P.C.J. Kamer, J.G. De Vries, and P.W.N.M. Van Leeuwen Eur. J. Inorg. Chem. 1999 1073 1076
43. In this study, kinetics on the Heck reaction of iodobenzene with styrene have shown that the oxidative addition step is not rate-limiting and consequently electron-withdrawing phosphites and phosphorus amidite are more active catalysts than triarylphosphines.
44. A.L. Casado, and P. Espinet J. Am. Chem. Soc. 120 1998 8978 8985
45. A.L. Casado, P. Espinet, A.M. Gallego, and J.M. Martinez-Ilarduya Chem. Commun. 2001 339 340
46. P. Espinet, and A.M. Echavarren Angew. Chem., Int. Ed. 43 2004 4704 4734
47. For a review very clear on this topic see: R.B. Bedford, C.S.J. Cazin, and D. Holder Coord. Chem. Rev. 248 2004 2283 2321
48. For a review very clear on this topic see: A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. 41 2002 4176 4211
49. Even if optimized conditions can be found upon systematic efforts on variation of the tandem base/solvent, the ratio of ligand, or the use of additives (see Ref. 22) the coupling reaction remains somewhat sluggish and the comparison with strong σ-donating ligands is, up to now, unfavourable.
50. R.B. Bedford, C.S.J. Cazin, and S.L. Hazelwood Angew. Chem., Int. Ed. 41 2002 4120 4122
51. R.B. Bedford, S.L. Hazelwood, M.E. Limmert, D.A. Albisson, S.M. Draper, P.N. Scully, S.J. Coles, and M.B. Hursthouse Chem. Eur. J. 9 2003 3216 3227
52. 3 as a base.
53. B. Åkermark, G. Åkermark, L.S. Hegedus, and K. Zetterberg J. Am. Chem. Soc. 103 1981 3037 3040
54. O. Kuhn, and H. Mayr Angew. Chem., Int. Ed. 38 1999 343 346 See also references therein
55. A. Vitagliano, and B. Åkermark J. Organomet. Chem. 349 1988 C22 C26
56. B. Crociani, S. Antonaroli, F. Di Bianca, L. Canovese, F. Visentin, and P. Uguagliati J. Chem. Soc., Dalton Trans. 1994 1145 1151
57. L. Canovese, F. Visentin, P. Uguagliati, F.D. Bianca, S. Antonaroli, and B. Crociani J. Chem. Soc., Dalton Trans. 1994 3113 3118
58. L. Canovese, F. Visentin, P. Uguagliati, B. Crociani, and F. Di Bianca Inorg. Chim. Acta 235 1995 45 50
59. L. Canovese, F. Visentin, G. Chessa, A. Niero, and P. Uguagliati Inorg. Chim. Acta 293 1999 44 52
60. A.A. Tolmachev, S.P. Ivonin, and A.M. Pinchuk Heteroat. Chem. 6 1995 407 412
61. J.J. Bishop, A. Davison, M.L. Katcher, D.W. Lichtenberg, R.E. Merrill, and J.C. Smart J. Organomet. Chem. 27 1971 241 249