Efficient dendritic diphosphino Pd(II) catalysts for the Suzuki reaction of chloroarenes

Organic Letters

Volumn 7, Issue 11, 2005, Pages 2253-2256

  Lemo, Julietta ^a   Heuzé, Karine ^a   Astruc, Didier ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENEBORONIC ACID; LEAD; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CATALYST; SUZUKI REACTION;

EID: 20644470924     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050645+     Document Type: Article

References (73)

1. (a) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and Dendrons: Concepts, Syntheses and Applications; Wiley-VCH: Weinheim, Germany, 2002.
2. (b) Newkome, G. R.; He, E.; Moorefield, C. N. Chem. Rev. 1999, 99, 1689.
3. (c) Dendrimers and Nanosciences; Chimie, C. R., Astruc, D., Eds.; Elsevier: New York, 2003; Vols. 8-10.
4. Seminal works: (a) Kleij, R. A.; van Leeuwen, P. W. N. M.; van der Made, A. W. EP 0456317, 1991; Chem. Abstr. 1992, 116, 129870.
5. For a review of van Leeuwen's work in this area, see ref 4a. (b) Brunner, H.; Fürst, J.; Ziegler, J. J. Organomet. Chem. 1993, 454.
6. (c) Brunner, H.; Bublak, P. Synthesis 1995, 36.
7. (d) Brunner, H.; Nat, G. Synthesis 1995, 423.
8. For a review of Brunner's pionering work in the area, see: Brunner, H. J. Organomet. Chem. 1995, 500, 39.
9. (e) Knapen, J. W. J.; van der Made, A. W.; deWilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659.
10. (f) Lee, J. J.; Ford, W. T. J. Am. Chem. Soc. 1994, 116, 3753.
11. (a) For the first recovery and reuse of dendritic catalysts, see Reetz's seminal work: Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int., Ed. Engl. 1997, 36, 1526.
12. (b) Brinkmann, N.; Giebel, D.; Lohmer, G.; Reetz, M. T.; Kragl, U. J. Catal. 1999, 783, 163.
13. (c) Ref 4a.
14. (d) Kreiter, R.; Kleij, A. W.; Klein Gebbink, R. J. M.; van Koten, G. In Dendrimers IV: Metal Coordination, Self-Assembly, Catalysis; Vögtle, F., Schalley, C. A., Eds.; Topics in Current Chemistry; Springer-Verlag: Berlin, 2001; pp 217 and 163.
15. (e) van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Rev. 2002, 102, 3717.
16. (a) Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M Angew. Chem., Int. Ed. 2001, 40, 1828.
17. (b) Astruc, D.; Chardac, F. Chem. Rev. 2001, 101, 2991.
18. (a) Synthesis of these dendrimers and Heck catalysis were reported by Reetz, et al. (ref 3a);
19. see also: (b) Heuzé, K.; Méry, D.; Gauss, D.; Astruc, D. Chem. Commun. 2003, 2274.
20. (c) Heuzé, K.; Méry, D.; Gauss, D.; Blais, J.-C.; Astruc, D. Chem. Eur. J. 2004, 10, 3936.
21. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
22. (b) Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4544.
23. (c) Hassan, J.; Sévignon, M.; Gozzi C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
24. (d) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
25. (e) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
26. (f) Suzuki, A. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, 2002; pp 53-106.
27. (g) Miura, M. Angew. Chem., Int. Ed. 2004, 43, 2201.
28. (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
29. (b) Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413.
30. (c) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
31. (d) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
32. (e) Yin, J.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162.
33. (f) Barder, T. E.; Buchwald, S. L. Org. Lett. 2004, 6, 2649.
34. (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387.
35. (b) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
36. (c) Netherton, M. R.; Dai, C.; Neuschütz, K.; Fu, G. C J. Am. Chem. Soc. 2001, 123, 10099.
37. (d) Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 13662.
38. (e) Kirshhoff, J. H.; Dai, C.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1945.
39. (f) Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 1340.
40. (a) Gstöttmayr, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1363.
41. (b) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866.
42. (c) Viciu, M. S.; Germaneau, R. F.; Navarro-Feraandez, O.; Stevens, E. D.; Nolan, S. P. Organometallics 2002, 21, 5470.
43. (d) Navarro, O.; Kelly, R. A., III; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194.
44. (e) Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173.
45. (f) Lebel, H.; Janes, M. K.; Charette, A. B.; Nolan, S. P. J. Am. Chem. Soc. 2004, 126, 5046.
46. (a) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Angew. Chem., Int. Ed. 2002, 41, 4120.
47. (b) Bedforf, R. B.; Hazelwood, S. L.; Limmert, M. E. Chem. Commun. 2002, 2610.
48. (c) Bedford, R. B.; Hazelwood, S. L.; Limmert, M. E.; Albisson, D. A.; Draper, S. M.; Scully, P. N.; Coles, S. J.; Hursthouse, M. B. Chem. Eur. J. 2003, 9, 3216.
49. (d) Bedford, R. B.; Blake, M. E.; Butts, C. P.; Holder, D. Chem. Commun. 2003, 466.
50. (e) Bedford, R. B.; Hazelwood, S. L.; Limmert, M. E. Organometallics 2003, 22, 1364.
51. (a) Reetz, M. T.; Breinbauer, R.; Wanninger, K. Tetrahedron Lett. 1996, 37, 4499.
52. (b) Bumagin, N, A.; Bykov, V. V. Tetrahedron 1997, 53, 14437.
53. (c) Shen, W. Tetrahedron Lett. 1997, 38, 5575.
54. (d) Bei, X.; Crevier, T.; Guram, A. S.; Jandeleit, B.; Powers, T. S.; Turner, H. W.; Uno, T.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 3855.
55. (e) Ishiyama, T.; Ishida, K.; Miyaura, N. Tetrahedron 2001, 57, 9813.
56. (f) Schnyder, A.; Indolese, A. F.; Studer, M.; Blaser, H.-U. Angew. Chem., Int. Ed. 2002, 41, 3668.
57. (g) Li, G. Y. J. Org. Chem. 2002, 67, 3643.
58. (h) Altenhoff, G.; Goddard, R.; Lehmann, C. W.; Glorius, F. Angew. Chem., Int. Ed. 2003, 42, 3690.
59. (i) Roca, F. X.; Richard, C. J. Chem. Commun. 2003, 3002.
60. (j) Datta, A.; Ebert, K.; Plenio, H. Organometallics 2003, 22, 4685.
61. (k) Li, J.-H.; Liu, W.-J. Org. Lett. 2004, 4, 2809.
62. (l) Zapf, A.; Jackstell, R.; Rataboul, F.; Reirmeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38.
63. (m) Özdemir, I.; Alici, B.; Gürbüz, N.; Çetinkaya, E.; Çetinkaya, B. J. Mol. Catal. A 2004, 37.
64. (n) Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; Williams, V. A.; Granados, P.; Singer, R. D. J. Org. Chem. 2005, 70, 161.
65. Méry, D.; Heuzé, K.; Astruc, D. Chem. Commun. 2003, 1934.
66. Dioxane, toluene, and DME were used, but the catalysts were not soluble enough to carry out the reaction.
67. Various bases were tested for the Suzuki reaction of iodobenzene with phenylboronic acid and catalyst 1a, and again the best base was unambiguously NaOH. For more details, see Supporting Information.
68. Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1619.
69. 2O, and NaOH (6 mmol), at 65 °C, with 1a (0.001 mol %) gave a 73% yield after 3 days.
70. 1H NMR spectrum shows the signal of the catalyst (see ref 5c for details of the characterizations of the catalysts) with the presence of aromatic signals of borate salts species (see ref 6). Indeed, the mass of the precipitate is twice that of the initially loaded catalyst.
71. Recycling procedure described in ref 17 was followed. In the first reaction cycle, the brown THF phase was separated, and then pentane was added. A black precipitate, insoluble in all solvents, fell out of the clear mother liquor, which confirms the formation of Pd black. No catalysis was found herewith in the second reaction cycle.
72. 19b failed due to the thermal instability: Gatard, S.; Nlate, S.; Cloutet, E.; Bravic, G.; Blais, J.-C., Astruc, D. Angew. Chem., Int. Ed. 2003, 42, 452.
73. (b) Gatard, S.; Kahlal, S.; Méry, D.; Nlate, S.; Cloutet, E.; Saillard, J.-Y.; Astruc, D. Organometallics 2004, 23, 1313.