Computational characterization of the role of the base in the Suzuki-Miyaura cross-coupling reaction

Journal of the American Chemical Society

Volumn 127, Issue 25, 2005, Pages 9298-9307

  Braga, Ataualpa A C ^a,c   Morgon, Nelson H ^c   Ujaque, Gregori ^a   Maseras, Feliu ^a,b  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^c UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CALCULATIONS; CATALYSIS; CATALYSTS; COMPUTATIONAL METHODS; PALLADIUM; PROBABILITY DENSITY FUNCTION;

CROSS-COUPLING REACTION; TRANSITION STATES; TRANSMETALATION;

REACTION KINETICS;

BORONIC ACID DERIVATIVE; BROMINE; HYDROXIDE; ORGANOBORON DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; GEOMETRY; MATHEMATICAL COMPUTING; MATHEMATICAL MODEL; SUZUKI REACTION;

ACID-BASE EQUILIBRIUM; BORONIC ACIDS; CATALYSIS; COMPUTER SIMULATION; CROSS-LINKING REAGENTS; HYDROXIDES; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 21244496290     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050583i     Document Type: Article

References (87)

1. Metal Catalyzed Cross-Coupling Reactions; Diederich, F., de Mejiere, A. Eds.; John Wiley & Sons: New York, 2004.
2. (a) Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
3. (b) Tamao, K.; Hiyama, T.; Negishi, E. J. Organomet. Chem. 2002, 653, 1.
4. Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
5. Cárdenas, D. J. Angew. Chem., Int. Ed. 2003, 42, 384.
6. (a) Suzuki, A.; Miyaura, N. Chem. Rev. 1995, 95, 2457.
7. (b) Suzuki, A J. Organomet. Chem. 1999, 576, 147.
8. (c) Suzuki, A. J. Organomet. Chem. 2002, 653, 83.
9. (a) Stanforth, S. P. Tetrahedron 1998, 54, 263.
10. (b) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
11. For cross-coupling reactions using other transition metals see, for instance: (a) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
12. (b) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
13. (c) Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. 2004, 346, 1525.
14. (a) Yin, J.; Rainka, P., Zhang, X.-X.; Buchwald S. L. J. Am. Chem. Soc. 2002, 124, 1162.
15. (b) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871.
16. (a) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
17. (b) Littke, A. F.; Dai, C.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 114, 4350.
18. (c) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
19. Chemler, S. R.; Trauner D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4544.
20. Farina, V. Adv. Synth. Catal. 2004, 346, 1553.
21. (a) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804.
22. (b) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194.
23. Gstöttmayr, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1363.
24. Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 112, 4315.
25. Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2003, 42, 6667.
26. (a) Denmark, S. E.; Sweis, R. F.; Wehrli, D. J. Am. Chem. Soc. 2004, 126, 4865.
27. (b) Denmark, S. E.; Sweis, R. F.; Wehrli, D. J. Am. Chem. Soc. 2004, 126, 4876.
28. Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553.
29. (a) Botella, L.; Nájera, C. Angew. Chem., Int. Ed. 2002, 41, 179.
30. (b) Nájera, C.; Gil-Moltó, J.; Karlström, S. Adv. Synth. Catal. 2004, 346, 1798.
31. (a) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.
32. (b) Amatore, C.; Bahsoun, A. A.; Jutand, A.; Meyer, G.; Ntepe, A. N.; Ricard, L. J. Am. Chem. Soc. 2003, 125, 4212.
33. (c) Jutand, A. Eur. J. Inorg. Chem. 2003, 2017.
34. Miyaura, N. J. Organomet. Chem. 2002, 653, 54.
35. (a) Senn, H. M.; Ziegler, T. Organometallics 2004, 23, 2980.
36. (b) Goossen, L. J.; Koley, D.; Hermann, H.; Thiel, W. Chem. Commun. 2004, 23, 2980.
37. Ananikov, V. P.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 2002, 124, 2839.
38. Osakada, K. In Fundamentals of Molecular Catalysis; Kurosawa, H., Yamamoto, A., Eds; Elsevier: Amsterdam, 2003.
39. (a) Miyaura, N.; Yamada, Y.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437.
40. (b) Miyaura, N.; Suginome, H.; Suzuki, A. Tetrahedron Lett. Ibid. 1981, 22, 127.
41. Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972.
42. Aliprantis, A. O.; Canary, J. W. J. Am. Chem. Soc. 1994, 116, 6985.
43. Smith, G. B.; Dezeny, G. C.; Hughes, D. L.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1994, 59, 8151.
44. Matos, K.; Soderquist, J. A. J. Org. Chem. 1998, 63, 461.
45. Ridgway, B. H.; Woerpel, K. A. J. Org. Chem. 1998, 63, 458.
46. Liebeskind, L. S.; Srogl J. J. Am. Chem. Soc. 2000, 122, 11260.
47. (a) Moreno-Mañas, M.; Pérez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
48. (b) Aramendia, M. A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592.
49. (a) Moriya, T.; Miyaura, N.; Suzuki, A. Synlett 1994, 149.
50. (b) Kakino, R.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2001, 74, 371.
51. (a) Computational Modelling of Homogeneous Catalysis; Lledós. A., Maseras, F., Eds.; Kluwer: Dordrecht, The Netherlands, 2002.
52. (b) Ujaque, G.; Maseras, F.; Lledós, A. J. Am. Chem. Soc. 1999, 121, 1317.
53. (a) Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508.
54. (b) Ishiyama, T.; Ahiko, T.; Miyaura, N. Tetrahedron Lett. 1996, 6889.
55. (c) Ishiyama, T.; Itoh, Y.; Kitano, T.; Miyaura, N. Tetrahedron Lett. 1997, 3447.
56. Sumimoto, M.; Iwane, N.; Takahama, T.; Sakaki, S. J. Am. Chem. Soc. 2004, 126, 10457.
57. (a) Cundari, T. R.; Deng, J.; Zhao, Y. J. Mol. Struct.: THEOCHEM 2003, 632, 121.
58. (b) Eberhardt, J. K.; Fröhlich, R.; Würthwein, E.-U. J. Org. Chem. 2003, 68, 6690.
59. (c) Kozuch, S.; Shaik, S.; Jutand, A.; Amatore, C. Chem.-Eur. J. 2004, 10, 3072.
60. (a) Albert, K.; Gisdakis, P.; Rösch, N. Organometallics 1998, 17, 1608.
61. (b) Sundermann, A.; Uzan, O.; Martin, J. M. L. Chem.-Eur. J. 2001, 7, 1703.
62. (c) von Schenck, H.; Akermark, B.; Svensson, M. Organometallics 2002, 21, 2248.
63. (d) Matsubara, T. Organometallics 2003, 22, 4297.
64. (e) Napolitano, E.; Farina, V.; Persico, M. Organometallics 2003, 22, 4030.
65. (f) Balcells, D.; Maseras, F.; Keay, B. A.; Ziegler, T. Organometallics 2004, 23, 2784.
66. (g) Amatore, C.; Jutand, A.; Lemaitre, J.; Ricard, J. L.; Kozuch, S.; Shaik, S. J. Organomet. Chem. 2004, 689, 3728.
67. (a) Lee, C.; Parr, R. G.; Yang, W. Phys. Rev. 1988, 37, B785.
68. (b) Becke, A. D. J. Phys. Chem. 1993, 98, 648.
69. (c) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
70. Frish, M. J.; et al. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
71. (a) Hay, P. J.; Wadt, W. R. J. Phys. Chem. 1985, 82, 299.
72. (b) Wadt, W. R.; Hay, P. J. J. Phys. Chem. 1985, 82, 284.
73. Höllwarth, A.; Böhme, M.; Dapprich, S.; Ehlers, A. W.; Gobbi, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 237.
74. (a) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Phys. Chem. 1972, 56, 2257.
75. (b) Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; Defrees, D. J.; Pople, J. A. J. Phys. Chem. 1982, 77, 3654.
76. Check, C. E.; Faust, T. O.; Bailey, J. M.; Wright, B. J.; Gilbert, T. M.; Sunderlin, L. S. J. Phys. Chem. A 2001, 105, 8111.
77. Clark, T.; Chandrasekhar, J.; Spitzangel, G. W.; Schelyer, P.v. R. J. Comput. Chem. 1983, 4, 294.
78. (a) Maseras, F.; Morokuma, K. J. Comput. Chem. 1995, 16, 1160.
79. (b) Vreven, T.; Morokuma, K. J. Comput. Chem. 2000, 21, 1419.
80. Rappe, A. K.; Casewit, C. J.; Colwell, D. S.; Goddard, W. A.; Skiff, W. N. J. Am. Chem. Soc. 1992, 114, 10024.
81. See also: (a) Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1665.
82. (b) Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373.
83. (c) Galardon, E.; Ramdeehul, S.; Brown, J. M.; Cowley, A.; Hii, K. K.; Jutand, A. Angew. Chem., Int. Ed. 2002, 41, 1760.
84. (d) Bedford, R. B.; Cazin, C. S. J. Organometallics 2003, 22, 987.
85. For a recent review see: Miura, M. Angew. Chem., Int. Ed. 2004, 43, 2201.
86. Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994.
87. Grushin, V. V.; Alper, H. Organometallics 1996, 15, 5242.