Aqueous-phase, palladium-catalyzed cross-coupling of aryl bromides under mild conditions, using water-soluble, sterically demanding alkylphosphines

Journal of Organic Chemistry

Volumn 69, Issue 23, 2004, Pages 7919-7927

  DeVasher, Rebecca B ^a   Moore, Lucas R ^a   Shaughnessy, Kevin H ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; CATALYSTS; HYDROPHILICITY; MIXTURES; ORGANIC SOLVENTS; PALLADIUM; PURIFICATION; REACTION KINETICS; SALTS; SOLUBILITY; SOLUTIONS; SYNTHESIS (CHEMICAL); TOLUENE;

BIPHASIC MIXTURES; LIGANDS; WATER SOLUBILITY;

CATALYSIS;

2 (DI TERT BUTYLPHOSPHINO)ETHYLTRIMETHYLAMMONIUM CHLORIDE; 4 (DI TERT BUTYLPHOSPHINO) N,N DIMETHYLPIPERIDINIUM CHLORIDE; ACETONITRILE; ACRYLIC ACID COPOLYMER; BROMINE DERIVATIVE; CHLORINE DERIVATIVE; DIFLUNISAL; ORGANIC SOLVENT; PALLADIUM; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SODIUM DERIVATIVE; TOLUENE; TRI (3 SULFONATOPHENYL)PHOSPHINE TRISODIUM; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; PURIFICATION; ROOM TEMPERATURE; SONOGASHIRA REACTION; SUZUKI REACTION;

EID: 8644224057     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048910c     Document Type: Article

References (77)

1. Anastas, P. T.; Kirchhoff, M. M. Acc. Chem. Res. 2002, 35, 686-694
2. Sheldon, R. A. CHEMTECH 1994, 24, 38-47.
3. Jiménez-González, C.; Curzons, A. D.; Constable, D. J. C.; Cunningham, V. Int. J. LCA 2004, 9, 114-121.
4. Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A: Chem. 2002, 182-183, 419-437.
5. Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692.
6. Curran, D. P. Angew. Chem., Int. Ed. Engl. 1998, 37, 1174-1196.
7. Leitner, W. Acc. Chem. Res. 2002, 35, 746-756.
8. Dzyuba, S. V.; Bartsch, R. A. Angew. Chem., Int. Ed. 2003, 42, 148-150.
9. Prajapati, D.; Gohain, M. Tetrahedron 2004, 60, 815-833.
10. Kuntz, E. G. CHEMTECH 1987, 17, 570-575.
11. Genêt, J. P.; Savignac, M. J. Organomet. Chem. 1999, 576, 305-317.
12. Joó, F. Acc. Chem. Res. 2002, 35, 738-745.
13. Manabe, K.; Kobayashi, S. Chem. Eur. J. 2002, 8, 4094-4101.
14. Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561.
15. Li, C.-J. Acc. Chem. Res. 2002, 35, 533-538.
16. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
17. Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449-7476.
18. Negishi, E.-i.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2017.
19. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
20. Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
21. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633-9695.
22. Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
23. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
24. Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852-860.
25. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
26. Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413-2416.
27. Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550-9561.
28. You, J.; Verkade, J. G. J. Org. Chem. 2003, 68, 8003-8007.
29. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369-4378.
30. Kirchhoff, J. H.; Dai, C.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1945-1947.
31. Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729-1731.
32. Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000.
33. Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580.
34. Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677-2678.
35. Stauffer, S. R.; Beare, N. A.; Stambuli, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4641-4642.
36. Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423-1426.
37. Gstöttmayr, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Drosche, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1363-1365.
38. Jørgensen, M.; Lee, S.; Liu, X.; Wolkowski, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 12557-12565.
39. Selvakumar, K.; Zapf, A.; Beller, M. Org. Lett. 2002, 4, 3031-3033.
40. Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053-4056.
41. Viciu, M. S.; Kissling, R. M.; Stevens, E. D.; Nolan, S. P. Org. Lett. 2002, 4, 2229-2231.
42. Bedford, R. B. Chem. Commun. 2003, 1787-1796.
43. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
44. Casalnuovo, A. L.; Calabrese, J. C. J. Am. Chem. Soc. 1990, 112, 4324-4330.
45. Beletskaya, I. P.; Cheprakov, A. V. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; John Wiley & Sons: New York, 2002; Vol. 2, pp 2957-3006.
46. Wüllner, G.; Jänsch, H.; Kannenberg, S.; Schubert, F.; Boche, G. Chem. Commun. 1998, 1509-1510.
47. Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757-2759.
48. Moore, L. R.; Shaughnessy, K. H. Org. Lett. 2004, 6, 225-228.
49. Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551-7554.
50. Wolf, C.; Lerebours, R. Org. Lett. 2004, 6, 1147-1150.
51. Botella, L.; Najera, C. Angew. Chem., Int. Ed. 2002, 41, 179-181.
52. Bedford, R. B.; Blake, M. E.; Butts, C. P.; Holder, D. Chem. Commun. 2003, 466-467.
53. Western, E. C.; Daft, J. R.; Johnson, E. M., II; Gannett, P. M.; Shaughnessy, K. H. J. Org. Chem. 2003, 68, 6767-6774.
54. Hannah, J.; Ruyle, W. V.; Jones, H.; Matzuk, K. W.; Kelly, K. W.; Witzel, B. E.; Holtz, W. J.; Houser, R. A.; Shen, T. Y.; Sarett, L. H.; Lotti, V. J.; Risley, E. A.; Van Arman, C. G.; Winter, C. A. J. Med. Chem. 1978, 21, 1093-1100.
55. Adamski-Werner, S. L.; Palaninathan, S. K.; Sacchettini, J. C.; Kelly, J. W. J. Med. Chem. 2004, 47, 355-374.
56. We found no significant difference in activity in TPPTS/Pd catalysts with L:Pd ratios of 2-3:1.
57. Dupuis, C.; Adiey, K.; Charruault, L.; Michelet, V.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 2001, 42, 6523-6526.
58. Genêt, J. P.; Linquist, A.; Blard, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443-1446.
59. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028.
60. Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717.
61. Amatore, C.; Blart, E.; Genêt, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829-6839.
62. Dibowski, H.; Scmidtchen, F. P. Tetrahedron Lett. 1998, 39, 525-528.
63. Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843-7846.
64. Quignard, F.; Larbot, S.; Goutaodier, S.; Choplin, A. J. Chem. Soc., Dalton Trans. 2002, 1147-1151.
65. Uozumi, Y.; Kobayashi, Y. Heterocycles 2003, 59, 71-74.
66. Novák, Z.; Szabó, A.; Répási, J.; Kotschy, A. J. Org. Chem. 2003, 68, 3327-3329.
67. Appukkuttan, P.; Dehaen, W.; Van der Eycken, E. Eur. J. Org. Chem. 2003, 4713-4716.
68. Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058-9064.
69. Hessler, A.; Stelzer, O.; Dibowski, H.; Worm, K.; Schmidtchen, F. P. J. Org. Chem. 1997, 62, 2362-2369.
70. Villemin, D.; Nechab, B. J. Chem. Res., Synop. 2000, 429-431.
71. Williams, D. B. G.; Lombard, H.; Holzapfel, C. Synth. Commun. 2001, 31, 2077-2081.
72. Beller, M.; Krauter, J. G. E.; Zapf, A. Angew. Chem., Int. Ed. 1997, 36, 772-774.
73. Kogan, V.; Aizenshtat, Z.; Popovitz-Biro, R.; Neumann, R. Org. Lett. 2002, 4, 3529-3532.
74. Botella, L.; Nájera, C. J. Organomet. Chem. 2002, 663, 46-57.
75. Giordano, C.; Coppi, L.; Minisci, F., U.S. Patent 5,312,975, May 17, 1994.
76. Jones, H.; Houser, R. W., U.S. Patent 4,225,730, September 30, 1980.
77. Rosso, V. W.; Lust, D. A.; Bernot, P. J.; Grosso, J. A.; Modi, S. P.; Rusowicz, A.; Sedergran, T. C.; Simpson, J. H.; Srivastava, S. K.; Humoroa, M. J.; Anderson, N. G. Org. Proc. Res. Dev. 1997, 1, 311-314.