The palladium-catalyzed cross-coupling reaction of carboxylic anhydrides with arylboronic acids: A DFT study

Journal of the American Chemical Society

Volumn 127, Issue 31, 2005, Pages 11102-11114

  Goossen, Lukas J ^a,b   Koley, Debasis ^a   Hermann, Holger L ^a   Thiel, Walter ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^b Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CATALYSIS; DISSOCIATION; MATHEMATICAL MODELS; PALLADIUM; PROBABILITY DENSITY FUNCTION;

CATALYTIC ACTIVITY; CATALYTIC CYCLES; CROSS-COUPLING REACTIONS; SUZUKI REACTIONS;

CARBOXYLIC ACIDS;

ACETIC ACID; BORON; BORONIC ACID DERIVATIVE; CARBOXYL GROUP; PALLADIUM COMPLEX; PALLADIUM DIPHOSPHINE; PHENYL GROUP; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC PARTICLE; CATALYSIS; CHEMICAL COMPOSITION; DENSITY FUNCTIONAL THEORY; ENERGY; PHASE TRANSITION; REACTION ANALYSIS; SUZUKI REACTION; THEORY;

EID: 23744446576     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052435y     Document Type: Article

References (73)

1. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
2. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
3. (c) Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2000, 611, 392.
4. (d) Suzuki, A. in Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany 1998; p. 49.
5. (a) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437.
6. (b) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972.
7. (c) Miyaura, N.; Suzuki, A. Org. Synth. 1990, 68, 130.
8. (d) Satoh, M.; Miyaura, N.; Suzuki, A. Chem. Lett. 1986, 1329.
9. (e) Miyaura, N.; Satoh, M.; Suzuki, A. Tetrahedron Lett. 1981, 22, 127.
10. Goossen, L. J. Chem. Commun. 2001, 7, 669.
11. (a) Goossen, L. J.; Ghosh, K. Angew. Chem., Int. Ed. 2001, 40, 3458.
12. (b) Goossen, L. J.; Ghosh, K. Eur. J. Org. Chem. 2002, 19, 3254.
13. (c) Goossen, L. J.; Winkel, L.; Döhring, A.; Ghosh, K.; Paetzold, J. Synlett 2002, 8, 1237.
14. (d) Goossen, L. J.; Ghosh, K. Chem. Commun. 2001, 20, 2084.
15. (e) Nagayama, K.; Shimizu, I.; Yamamoto, A. Chem. Lett. 1998, 1143.
16. (f) Kakino, R.; Kamusi, S.; Shimizu, L; Yamamoto, A. Bull. Chem. Soc. Jpn. 2002, 75, 137.
17. (a) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.
18. (b) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 1670.
19. (c) Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531.
20. (d) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009.
21. (e) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A.; Meyer, G. Organometallics 1995, 14, 5605.
22. (a) Goossen, L. J.; Koley, D.; Hermann, H.; Thiel, W. Chem. Commun. 2004, 2141.
23. (b) Goossen, L. J.; Koley, D.; Hermann, H.; Thiel, W. Organometallics 2005, 24, 2398.
24. (a) Kozuch, S.; Shark, S.; Jutand, A.; Amatore, C. Chem.-Eur. J. 2004. 10, 3072.
25. (b) Kozuch, S.; Amatore, C.; Jutand, A.; Shaik, S. Organometallics 2005, 24, 2319.
26. Sundermann, A.; Uzan, O.; Martin, J. M. L. Chem.-Eur. J. 2001, 7, 1703.
27. (a) Hills, I. D.; Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5749.
28. (b) Eberhardt, J. K.; Fröhlich, R.; Würthwein, E.-U. J. Org. Chem. 2003, 68, 6690.
29. (a) Cui, Q.; Musaev, D. G.; Morokuma, K. Organometallics 1998, 17, 1383 and references therein.
30. (b) Dorico, A. E.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 115.
31. (a) Albert, K.; Gisdakis, P.; Rösch, N. Organometallics 1998, 17, 1608.
32. (b) Deeth, R. J.; Smith, A.; Brown, J. M. J. Am. Chem. Soc. 2004, 126, 7144.
33. (c) Balcells, D.; Maseras, F.; Keay, B. A.; Ziegler, T. Organometallics 2004, 23, 2784.
34. (d) Deeth, R. J.; Smith, A.; Hu, K. K.; Brown, J. M. Tetrahedron Lett. 1998, 39, 3229.
35. (e) Hii, K. K.; Claridge, T. D. W.; Brown, J. M.; Smith, A.; Deeth, R. J. Helv. Chim. Acta 2001, 84, 3043.
36. (f) von Schenck, H.; Akcrmark, B.; Svensson, M. J. Am. Chem. Soc. 2003, 125, 3503.
37. (g) Ludwig, M.; Stromberg, S.; Svensson, M.; Akermark, B. Organometallics 1999, 18, 970.
38. (a) Nagayama, K.; Kawataka, F.; Sakamoto, M.; Shimizu, I.; Yamamoto, A. Chem. Lett. 1995, 367.
39. (b) Kakino, R.; Narahashi, H.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2002, 75, 1333.
40. Jutand, A.; Négri, S.; de Vries, J. G. Eur. J. Inorg. Chem. 2002, 1711.
41. 2 or a base (Juland, A. private communication, 2005).
42. Frisch, M. J. et al. Gaussian 03, revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.
43. Becke, A. D. Phys. Rev. A 1988, 33, 3098.
44. Perdew, J. P. Phys. Rev. B 1986, 33, 8822.
45. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
46. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
47. Andrae, D.; Häussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta 1990, 77, 123.
48. (a) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995.
49. (b) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669.
50. (a) Klamt, A.; Schüürmann, G. J. Chem. Soc., Perkin Trans. 2 1993, 799.
51. (b) Schäfer, A.; Klamt, A.; Sattel, D.; Lohrenz, J. C. W.; Eckert, F. Phys. Chem. Chem. Phys. 2000, 2, 2187.
52. (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
53. (b) Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO, version 3.1.
54. (a) Basolo, F.; Pearson, G. Mechanism of Inorganic Reactions, 2nd ed.; Wiley: New York, 1967.
55. (b) Huheey, J. E.; Keiter, E. A.; Keiter, R. L. Inorganic Chemistry: Principles of Structures and Reactivity, 4th ed.; Harper-Collins College Publishers: New York, 1993.
56. (a) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978.
57. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954.
58. (c) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
59. (d) Casares, J. A.; Espinet, P.; Salas, G. Chem.-Eur. J. 2002, 8, 4843.
60. Miyaura, N. J. Organomet. Chem. 2002, 653, 54 and references therein.
61. Napolitano, E.; Farina, V.; Persico, M. Organometallics 2003, 22, 4030 and references therein.
62. Louie, J.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11598.
63. Moriya, T.; Miyaura, N.; Suzuki, A. Synlett 1994, 149.
64. 3 to yield another van der Waals adduct 4c, and subsequent coordination of acetate to generate 5. The corresponding data are included in the Supporting Information.
65. Goossen, L. J.; Koley, D.; Hermann, H.; Thiel, W. Manuscript in preparation.
66. 2 hydrogen bonds were calculated to be -9.4 and -10.7 kcal/mol, respectively. See the Supporting Information for details.
67. Matos, K.; Sonderquist, J. A. J. Org. Chem. 1998, 63, 461.
68. Senn, H. M.; Ziegler, T. Organometallics 2004, 23, 2980.
69. (a) Farina, V.; Krisnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
70. (b) Farina, V.; Roth, G. P. Recent Advances in the Stille Reaction. In Adv. Metalorg. Chem. 1996, 5, 1.
71. (c) Amatore, C.; Bahsoun, A.; Jutand, A.; Meyer, G.; NdediNtepe, A.; Ricard, L. J. Am. Chem. Soc. 2003, 125, 4212.
72. (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
73. (b) Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999. 38, 2413.