On the mechanistic behavior of highly efficient palladium-tetraphosphine catalytic systems for cross-coupling reactions: First spectroscopic and electrochemical studies of oxidative addition on Pd(0)/multidentate ferrocenylpolyphosphine complexes

Organometallics

Volumn 27, Issue 11, 2008, Pages 2643-2653

  Evrard, D ^a   Lucas, D ^a   Mugnier, Y ^a   Meunier, P ^a   Hierso, J C ^a  

^a UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; PALLADIUM;

CATALYTIC SYSTEMS; CROSS-COUPLING REACTIONS; ELECTROCHEMICAL STUDIES; HIGHLY EFFICIENT; MULTIDENTATE; OXIDATIVE ADDITION (OA); TETRAPHOSPHINE;

PALLADIUM COMPOUNDS;

EID: 45449084660     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om701279x     Document Type: Article

References (78)

1. For reviews on palladium-based cross-coupling reactions see: (a) Doucet, H.; Hierso, J.-C. Angew. Chem., Int. Ed. 2007, 46, 834-871.
2. (b) Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651-2710.
3. (c) Christmann, U.; Vilar, R. Angew. Chem., Int. Ed. 2005, 44, 366-374.
4. (d) Zapf, A.; Beller, M. Chem. Commun. 2005, 431-440.
5. (e) Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527-2571.
6. (f) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442-4489.
7. (g) Beletskaya, I. P.: Cheprakov, A. V. J. Organomet. Chem. 2004, 689, 4055-4082.
8. (h) Farina, V. Adv. Synth. Catal. 2004, 346, 1553-1582.
9. (i) Bedford, R. B.; Cazin, C. S. J.; Holder, D. Coord. Chem. Rev. 2004, 248, 2283-2321.
10. (j) Negishi, E.-I.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2017.
11. (k) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
12. (a) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 13944-13945.
13. (b) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 1232-1233.
14. (c) Stambuli, J. P.; Incarvito, C. D.; Bühl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 1184-1194.
15. (a) Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 3910-3912.
16. (b) Hills, I. D.; Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 41, 5749-5752.
17. (c) Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 13178-13179.
18. (a) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375-8384.
19. (b) Amatore, C.; Jutand, A. J. Organomet. Chem. 1999, 576, 254-278.
20. (c) Amatore, C.; Bucaille, A.; Fuxa, A.; Jutand, A.; Meyer, G.; Ndedi Ntepe, A. Chem.-Eur. J. 2001, 7, 2134-2142.
21. (a) Hierso, J.-C.; Beaupérin, M.; Meunier, P. Eur. J. Inorg. Chem. 2007, 3767-3780.
22. (b) Hierso, J.-C.; Smaliy, R. V.; Amardeil, R.; Meunier, P. Chem. Soc. Rev. 2007, 36, 1754-1769.
23. (a) Hierso, J.-C.; Fihri, A.; Amardeil, R.; Meunier, P.; Doucet, H.; Santelli, M.; Donnadieu, B. Organometallics 2003, 22, 4490-4499.
24. (b) Hierso, J.-C.; Fihri, A.; Amardeil, R.; Meunier, P.; Doucet, H.; Santelli, M.; Ivanov, V. V. Org. Lett. 2004, 6, 3473-3476.
25. (c) Nguyen, D. H.; Urrutigoïty, M.; Fihri, A.; Hierso, J.-C.; Meunier, P.; Kalck, P. Appl. Organomet. Chem. 2006, 20, 845-850.
26. (d) Feuerstein, M.; Doucet, H.; Santelli, M. Synlett 2001, 1458-1460.
27. (e) Laurenti, D.; Feuerstein, M.; Pèpe, G.; Doucet, H.; Santelli, M. J. Org. Chem. 2001, 66, 1633-1637.
28. (f) Doucet, H.; Santelli, M. Synlett 2006, 1-15.
29. (g) Schill, H.; de Meijere, A.; Yufit, D. S. Org. Lett. 2007, 9, 2617-2620.
30. (h) Kondolff, I.; Feurstein, M.; Doucet, H.; Santelli, M. Tetrahedron 2007, 63, 9514-9521.
31. (a) Broussier, R.; Bentabet, E.; Amardeil, R.; Richard, P.; Meunier, P.; Kalck, P.; Gautheron, B. J. Organomet. Chem. 2001, 637-639, 126-133.
32. (b) Broussier, R.; Bentabet, E.; Mellet, P.; Blacque, O.; Boyer, P.; Kubicki, M.; Gautheron, B. J. Organomet. Chem. 2000, 595, 365-373.
33. Hierso, J.-C.; Fihri, A.; Ivanov, V. V.; Hanquet, B.; Pirio, N.; Donnadieu, B.; Rebière, B.; Amardeil, R.; Meunier, P. J. Am. Chem. Soc. 2004, 126, 11077-11087.
34. NMR spectra (and g-NMR simulation for lb) and X-ray data are available as Supporting Information.
35. (a) Barrière, F.; Kirss, R. U.; Geiger, W. E. Organometallics 2005, 24, 48-52, and references therein.
36. (b) Fihri, A.; Hierso, J.-C.; Meunier, P. Coord. Chem. Rev. 2007, 251, 2017-2055.
37. (a) Miller, T. M.; Ahmed, K. J.; Wrighton, M. S. Inorg. Chem. 1989, 28, 2347-2355.
38. (b) Pilloni, G.; Longato, B.; Corain, B. J. Organomet. Chem. 1991, 420, 57-65.
39. (c) Gref, A.; Diter, P.; Guillaneux, D.; Kagan, H. B. New J. Chem. 1997, 21, 1353-1358.
40. (a) Corain, B.; Longalo, B.; Favero, G.; Ajò, D.; Pilloni, G.; Russo, U.; Kreiss, F. R. Inorg. Chim. Acta 1989, 157, 259-261.
41. (b) Nataro, C.; Campbell, A. N.; Ferguso, M. A.; Incarvita, C. D.; Rheingold, A. L. J. Organomet. Chem. 2003, 673, 47-55.
42. Mugnier, Y.; Moïse, C.; Tirouflet, J.; Laviron, E. J. Organomet. Chem. 1980, 186, C49-C52.
43. 2) group is 0.19; see: Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
44. Voltammetric investigation of the electrolyzed solution shows that peak O is observed in the first anodic scan (Figure 4, line b). Noticeably, the backward cathodic scan makes reduction peak R happen: the electrolysis product can be converted back to la by oxidation.
45. For a review see: Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314-321.
46. Amatore, C.; Azzabi, M.; Jutand, A. J. Organomet. Chem. 1989, 363, C41-C45.
47. 3 similarly displays in the cathodic scan a two-electron chemically irreversible reduction around-1 V vs SCE, which is coupled upon scan inversion to an oxidation O more positive than R by nearly 1 V.
48. This case is much more probable because of the simplicity of the voltammograms and NMR spectra obtained.
49. 0 species; see ref 4a. However, the values of phosphorus chemical shift are not really in favor of this hypothesis compared to data reported by Jutand and Amatore and also to the other NMR chemical shifts obtained in the presence of excess halides.
50. Fairlamb, I. J. S.; Kapdi, A. R.; Lee, A. F.; McGlackpen, G. P.; Weissburger, F.; Fries, A. H. M.; Schmieder-van de Vondervoort, L. Chem.-Eur. J. 2006, 12, 8750-8761.
51. (a) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704-4734.
52. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
53. (c) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1995, 33, 2379-2411.
54. (d) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
55. (e) Stille, J. K.; Lau, K. S. Y. Acc. Chem. Res. 1977, 10, 434-442.
56. (f) Ariafard, A.; Lin, Z. Organometallics 2006, 25, 4030-4033, and references therein.
57. (g) Goossen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. Organometallics 2005, 24, 2938-2410.
58. See for instance the discussion in: Hierso, J.-C.; Fihri, A.; Amardeil, R.; Meunier, P.; Doucet, H.; Santelli, M. Tetrahedron 2005, 61, 9759-9766, and references therein.
59. (a) Barrios-Landerros, F.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 6944-6945.
60. (b) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 8704-8705.
61. (c) Stambuli, J. P.; Bühl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9346-9347.
62. (d) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 1120, 8978-8985.
63. (e) Casado, A. L.;. Espinet, P. Organometallics 1998, 17, 954-959.
64. (f) Jutand, A.; Mosleh, A. Organometallics 1995, 14, 1810-1817.
65. (g) Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373-5374.
66. (h) Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030-3039.
67. (i) Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531-9541.
68. (j) Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1665-1673.
69. (k) Amatore, C.; Pflüger, F. Organometallics 1990, 9, 2276-2282.
70. norm,O = 50%.
71. Macé, Y.; Kapdi, A. R.; Fairlamb, I. J. S.; Jutand, A. Organometallics 2006, 25, 1795-1800.
72. (a) Amatore, C.; Broeker, G.; Jutand, A.; Khalil, F. J. Am. Chem. Soc. 1997, 119, 5176-5185.
73. (b) Alcazar-Roman, L. M.; Hartwig, J. F.; Rheingold, A. L.; Liable-Sands, L. M.; Guzei, I. A. J. Am. Chem. Soc. 2000, 122, 4618-4630.
74. arom-X bond; see ref 27.
75. The exchange energy barrier from A′ to A″ is expected to be rather low.
76. (a) Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purifications of Laboratory Chemicals; Pergamon Press: Oxford, 1966.
77. (b) Gordon, A. J.; Ford, R. A. The Chemist's Companion, a Handbook of Practical Data, Techniques and References; Wiley: New York, 1972; p 436.
78. Schultz, R. G. J. Organomet. Chem. 1966, 6, 435-436.