Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates

Journal of Organic Chemistry

Volumn 68, Issue 11, 2003, Pages 4302-4314

  Molander, Gary A ^a   Biolatto, Betina ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS COUPLING REACTIONS;

CATALYSIS; ELECTRONS; PALLADIUM; POTASSIUM COMPOUNDS;

ORGANIC COMPOUNDS;

BORIC ACID; BROMIDE; CHLORIDE; FLUORINE DERIVATIVE; PALLADIUM; POTASSIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038362703     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0342368     Document Type: Article

References (85)

1. (a) Tsuji, J. Palladium Reagents and Catalysis; Wiley and Sons: Chichester, UK, 1995.
2. (b) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; VCH: Weinheim, Germany, 1998.
3. (c) Cross-Coupling Reactions. A Practical Guide. In Topics in Current Chemistry; Miyaura, N., Vol. Ed.; Springer-Verlag: Berlin, Germany, 2002; Vol. 219.
4. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
5. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
6. For reviews see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
7. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
8. (c) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; VCH: Weinheim, Germany, 1998; pp 49-97.
9. (d) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469.
10. (a) Giovannini, R.; Knochel, P. J. Am. Chem. Soc. 1998, 120, 11186-11187.
11. (b) Lipshutz, B. H.; Blomgren, P. A. J. Am. Chem. Soc. 1999, 121, 5819-5820.
12. (c) Piber, M.; Jensen, A. E.; Rottländer, M.; Knochel, P. Org. Lett. 1999, 1, 1323-1326.
13. (d) Lipshutz, B. H.; Blomgren, P. A.; Kim, S.-K. Tetrahedron Lett. 1999, 40, 197-200.
14. (e) Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719-2724.
15. (a) Kabalka, G. W.; Pagni, R. M.; Hair, C. M. Org. Lett. 1999, 1, 1423-1425.
16. (b) Kabalka, G. W.; Namboodiri, V.; Wang, L. Chem. Commun. 2001, 775.
17. (c) LeBlond, C. R.; Andrews, A. T.; Sun, Y.; Sowa, J. R., Jr. Org. Lett. 2001, 3, 1555-1557.
18. (d) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721-2722.
19. (e) Campi, E. M.; Jackson, W. R.; Marcuccio, S. M.; Naeslund, C. G. M. Chem. Commun. 1994, 2395.
20. (f) Darses, S.; Jeffery, T.; Genêt, J.-P.; Brayer, J.-L.; Demoute, J.-P. Tetrahedron Lett. 1996, 37, 3857-3860.
21. (g) Bumagin, N. A.; Bykov, V. V. Tetrahedron 1997, 53, 14437-14450.
22. (h) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170-7173.
23. (i) Goodson, E. F.; Wallow, T. I.; Novak, B. M. Org. Synth. 1998, 75, 61-68.
24. (j) Blettner, C. G.; König, W. A.; Stenzel, W.; Schotten, T. J. Org. Chem. 1999, 64, 3885-3890.
25. (k) Bussolari, J. C.; Rehborn, D. C. Org. Lett. 1999, 1, 965-967.
26. (l) Chi, S. M.; Choi, J.-K.; Yum, E. K.; Chi, D. Y. Tetrahedron Lett. 2000, 41, 919-922.
27. (m) Zin, D.; Monteiro, A. L.; Dupont, J. Tetrahedron Lett. 2000, 41, 8199-8202.
28. (n) Ma, D.; Wu, Q. Tetrahedron Lett. 2001, 42, 5279-5281.
29. (a) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866-2873 and references therein.
30. (b) Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. J. Org. Chem. 1999, 64, 6797-6803.
31. (c) Yin, J.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162-1163.
32. (d) Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820-3827.
33. (e) Feuerstein, M.; Berthiol, F.; Doucet, H.; Santelli, M. Synlett 2002, 1807-1810 and references therein.
34. (a) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677-8681.
35. (b) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553-5566.
36. (c) Liu, S.-Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408-2409.
37. (d) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997-3000 and references therein.
38. (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 37, 3387-3388.
39. (b) Littke, A. F.; Chaoyang, D.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028.
40. (a) Roques, B. P.; Florentin, D.; Callanquin, M. J. Heterocycl. Chem. 1975, 12, 195-196.
41. (b) Florentin, D.; Fournié-Zaluski, M. C.; Callanquin, M.; Roques, B. P. J. Heterocycl. Chem. 1976, 13, 1265-1272.
42. (c) Kuivila, H. G.; Nahabedian, K. V. J. Am. Chem. Soc. 1961, 83, 2159-2163.
43. Moreno-Mañas, M.; Pérez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346-2351 and references therein.
44. Wong, M. S.; Zhang, X. L. Tetrahedron Lett. 2001, 42, 4087-4089.
45. (a) Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3020-3027.
46. (b) Vedejs, E.; Fields, S. C.; Hayashi, R.; Hitchcock, S. R.; Powell, D. R.; Schrimpf, M. R. J. Am. Chem. Soc. 1999, 121, 2460-2470.
47. (a) Darses, S.; Jeffery, T.; Brayer, J.-L.; Demoute, J.-P.; Genêt, J.-P. Bull. Soc. Chim Fr. 1996, 133, 1095-1102.
48. (b) Darses, S.; Brayer, J.-L.; Demoute, J.-P.; Genêt, J.-P. Tetrahedron Lett. 1997, 38, 4393-4396.
49. (c) Darses, S.; Michaud, G.; Genêt, J.-P. Eur. J. Org. Chem. 1999, 1875-1883.
50. Chen, Z.-C.; Xia, M. Synth. Commun. 1999, 29, 2457-2465.
51. Molander, G. A.; Biolatto, B. Org. Lett. 2002, 4, 1867-1870.
52. Batey, R. A.; Quach, T. D. Tetrahedron Lett. 2001, 42, 9099-9103.
53. (a) Molander, G. A.; Rodriguez Rivero, M. Org. Lett. 2002, 4, 107-109.
54. (b) Molander, G. A.; Bernardi, C. R. J. Org. Chem. 2002, 67, 8424-8429.
55. (a) Molander, G. A.; Ito, T. Org. Lett. 2001, 3, 393-396.
56. (b) Molander G. A.; Katona, B. W.; Machrouhi, F. J. Org. Chem. 2002, 67, 8416-8423.
57. Feuerstein, M.; Laurenti, D.; Bougenat, C.; Doucet, H.; Santelli, M. Chem. Commun. 2001, 325-326.
58. The reaction between the corresponding diazonium salt and phenyltrifluoroborate was performed under ligandless conditions with similar results. See ref 13a.
59. Ligands containing amine moieties have proved to provide active catalysts for Suzuki couplings when a phosphine group is also present in the molecule: Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 12051-12052. Other N-containing ligands, for example, bis-(pyrimidyl)-based palladium complexes, do not show a high efficiency in Suzuki couplings: Buchmeiser, M. R.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39-46.
60. Ligands containing amine moieties have proved to provide active catalysts for Suzuki couplings when a phosphine group is also present in the molecule: Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 12051-12052. Other N-containing ligands, for example, bis-(pyrimidyl)-based palladium complexes, do not show a high efficiency in Suzuki couplings: Buchmeiser, M. R.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39-46.
61. 4NBr to produce quantitative yields. See ref 5f.
62. Villemin, D.; Caillot, F. Tetrahedron Lett. 2001, 42, 639-642.
63. 2 have been used to perform the homocoupling of both electron-poor and electron-rich arylboronic acids. See ref 11.
64. Thiemann, T.; Umeno, K.; Ohira, D.; Inohae, E.; Sawada, T.; Mataka, S. New J. Chem. 1999, 23, 1067-1070.
65. Frohn, H.-J.; Adonin, N. Y.; Bardin, V. V.; Starichenko, V. F. Tetrahedron Lett. 2002, 43, 8111-8114.
66. Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314-321.
67. (a) Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 207-210.
68. (b) Castanet, A.-S.; Colobert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry 2002, 13, 659-665 and references therein.
69. Colacot, T. J.; Gore, E. S.; Kuber, A. Organometallics 2002, 21, 3301-3304.
70. It has been shown that 3-bromothiophene requires special ligands to afford good yields of coupling products. Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2001, 42, 5659-5662.
71. McCarthy, M.; Gury, P. J. Tetrahedron 1999, 55, 3061-3070.
72. Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R. A.; Wallbank, P. J. Tetrahedron 1992, 48, 8117-8126.
73. 3, in DME-water, affording 72% yield of product after heating at reflux overnight. Gronowitz, S.; Hoernfeldt, A. B.; Kristjansson, V.; Musil, T. Chem. Scr. 1986, 26, 305-309.
74. The cross-coupling and homocoupling products are highly sensitive to light and sublime at room temperature, accounting for the low recovery of product.
75. Different pyrazoles have been employed as nonchelating and chelating ligands. Grotjahn, D. B.; Van, S.; Combs, D.; Lev, D. A.; Schneider, C.; Rideout, M.; Meyer, C.; Hernandez, G.; Mejorado, L. J. Org. Chem. 2002, 67, 9200-9209.
76. Trichloropyrimidine is known to undergo nucleophilic substitution by phenolate ions. Delia, T. J.; Nagarajan, A. J. Heterocycl. Chem. 1998, 35, 269-273. Whether the palladium catalyst plays a role in favoring this reaction under our conditions is not known.
77. Several byproducts arising from substitution of the chlorine atoms by ethoxy groups and/or coupling with the aryltrifluoroborates were detected by GC-MS analysis, in trace levels, which accounts for the conversion of the remaining 20-30% of halide 2ac, for entries 2-4, Table 9.
78. Schomaker, J. M.; Delia, T. J. J. Org. Chem. 2001, 66, 7125-7128.
79. Gronowitz, S.; Peters, D. Heterocycles 1990, 30, 645-58.
80. Under these conditions, the reactions with the more electron deficient methyl 5-bromonicotinate afford high yields of products after 2-6 h. (a) Thompson, W. J.; Gaudino, J.J. Org. Chem. 1984, 49, 5237-5243. (b) Thompson, W. J.; Jones, J. H.; Lyle, P. A.; Thies, J. E. J. Org. Chem. 1988, 53, 2052-2055.
81. Under these conditions, the reactions with the more electron deficient methyl 5-bromonicotinate afford high yields of products after 2-6 h. (a) Thompson, W. J.; Gaudino, J.J. Org. Chem. 1984, 49, 5237-5243. (b) Thompson, W. J.; Jones, J. H.; Lyle, P. A.; Thies, J. E. J. Org. Chem. 1988, 53, 2052-2055.
82. Sindkhedkar, M. D.; Mulla, H. R.; Wurth, M. A.; Cammers-Goodwin, A. Tetrahedron 2001, 57, 2991-2996.
83. 3, and then allowed to warm to room temperature overnight. The solvent was evaporated, and volatile impurities were removed as an azeotrope with dry MeOH.
84. Matos, K.; Soderquist, J. A. J. Org. Chem. 1998, 63, 461-470.
85. Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550-9561.