Mechanism of Palladium-Catalyzed Cross-Coupling Reactions

Computational Modeling for Homogeneous and Enzymatic Catalysis: A Knowledge-Base for Designing Efficient Catalysts

Volumn , Issue , 2008, Pages 109-130

  Braga, Ataualpa A C ^a   Ujaque, Gregori ^b   Maseras, Feliu ^a  

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

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

Computational modeling; Enzymatic catalysis; Homogenous catalysis; Isomerization; Oxidative addition; Palladium catalyzed cross coupling reactions; Reductive elimination; Transmetalation

Indexed keywords

EID: 84889867539     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527621965.ch5     Document Type: Chapter

References (60)

1. nd ed., Wiley-VCH, Weinheim, 2004.
2. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
3. J. K. Stille, Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524.
4. E. Negishi, L. Anastasia, Chem. Rev. 2003, 103, 1979-2017.
5. I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066.
6. K. Sonogashira, J. Organomet. Chem. 2002, 653, 46-49.
7. J. F. Hartwig, M. Kawatsura, S. I. Hauck, K. H. Shaughnessy, L. M. Alcazar-Roman, J. Org. Chem. 1999, 64, 5575-5580.
8. A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 219, 131-209.
9. A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 2002, 22, 4176-4221.
10. nd edn., eds. A. De Meijere, F. Diederich, Wiley-VCH, Weinheim, 2004, pp. 1-39.
11. P. Espinet, A. M. Echavarren, Angew. Chem. Int. Ed. 2004, 43, 4704-4734.
12. C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321.
13. L. J. Goossen, D. Koley, H. L. Hermann, W. Thiel, J. Am. Chem. Soc. 2005, 125, 11102-11114.
14. L. J. Goossen, D. Koley, H. L. Hermann, W. Thiel, Organometallics 2006, 25, 5467.
15. A. A. C. Braga, G. Ujaque, F. Maseras, Organometallics 2006, 25, 3647-3658.
16. R. Alvarez, O. N. Faza, C. S. Lopez, A. R. de Lera, Org. Lett. 2006, 8, 35-38.
17. J. O. Noell, P. J. Hay, J. Am. Chem. Soc. 1982, 104, 4578-4584.
18. J. J. Low, W. A. Goddard, J. Am. Chem. Soc., 1984, 106, 6928-6937.
19. S. Obara, K. Kitaura, K. Morokuma, J. Am. Chem. Soc., 1984, 106, 7482-7492.
20. S. Sakaki, N. Mizoe, Y. Musahi, B. Biswas, M. J. Sugimoto, J. Phys. Chem. A, 1998, 102, 8027-8036.
21. T. Matsubara, K. Hirao, Organometallics 2002, 21, 4482-4489.
22. H. M. Senn, T. Ziegler, Organometallics 2004, 23, 2980-2988.
23. A. Sundermann, J. M. L. Martin, Chem. Eur. J. 2001, 7, 1703-1711.
24. S. Kozuch, C. Amatore, A. Jutand, S. Shaik, Organometallics 2005, 24, 2319-2330.
25. A. Diefenbach, G. T. de Jong, F. M. Bickelhaupt, J. Chem. Theory Comput. 2005, 1, 286-298.
26. L. J. Goossen, D. Koley, H. L. Hermann, W. Thiel, Organometallics 2005, 24, 2398-2410.
27. J. F. Hartwig, F. Paul, J. Am. Chem. Soc. 1995, 117, 5373-5374.
28. A. G. Littke, C. Y. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020-4028.
29. T. R. Cundari, J. Deng, J. Phys. Org. Chem. 2005, 18, 417-425.
30. M. Ahlquist, P. Fristrup, D. Tanner, P.-O. Norrby, Organometallics 2006, 25, 2066-2073.
31. M. Ahlquist, P.-O. Norrby, Organometallics 2007, 26, 550-553.
32. A. Ariafard, Z. Lin, Organometallics 2006, 25, 403-4033.
33. D. Balcells, F. Maseras, B. A. Keay, T. Ziegler, Organometallics 2004, 23, 2784-2796.
34. D. L. Davies, S. M. A. Donald, S. A. Macgregor, J. Am. Chem. Soc. 2005, 127, 13754-13755.
35. D. García-Cuadrado, A. A. C. Braga, F. Maseras, A. M. Echavarren, J. Am. Chem. Soc. 2006, 128, 1066-1067.
36. N. Miyaura, J. Organomet. Chem. 2002, 653, 54-57.
37. A. A. C. Braga, N. H. Morgon, G. Ujaque, F. Maseras, J. Am. Chem. Soc. 2005, 127, 9298-9307.
38. L. S. Hegedus, Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill Valley, CA, 1994.
39. N. Miyaura, Y. Yamada, H. Suginome, A. Suzuki, J. Am. Chem. Soc. 1985, 107, 972-980.
40. A. A. C. Braga, N. H. Morgon, G. Ujaque, A. Lledos, F. Maseras, J. Organomet. Chem. 2006, 691, 4459-4466.
41. K. Osakada, Fundamentals of Molecular Catalysis, eds. H. Kurosawa, A. Yamamoto, Elsevier, Amsterdam, 2003, pp. 233-291.
42. S. Kozuch, S. Shaik, A. Jutand, C. Amatore, Chem. Eur. J. 2004, 10, 3072-3080.
43. J. Louie, J. F. Hartwig, J. Am. Chem. Soc. 1995, 117, 11598-11599.
44. F. Barrios-Landeros, J. F. Hartwig, J. Am. Chem. Soc. 2005, 127, 6944-6945.
45. J. P. Stambuli, M. Bühl, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 9346-9347.
46. T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685-4696.
47. U. Christmann, R. Vilar, Angew. Chem. Int. Ed. 2005, 44, 366-374.
48. M. Sumimoto, N. Iwane, T. Takahama, S. Sakaki, J. Am. Chem. Soc. 2004, 126, 10457-10471.
49. A. L. Casado, P. Espinet, J. Am. Chem. Soc. 1998, 120, 8978-8985.
50. A. L. Casado, P. Espinet, A. M. Gallego, J. Am. Chem. Soc. 2000, 122, 11771-11782.
51. V. Farina, B. Krishnan, D. R. Marshall, G. P. Roth, J. Org. Chem. 1993, 58, 5434-5444.
52. A. L. Casado, P. Espinet, A. M. Gallego, J. M. Martínez-Ilarduya, Chem. Comunn. 2001, 339-340.
53. A. Nova, G. Ujaque, F. Maseras, A. Lledoís, P. Espinet, J. Am. Chem. Soc. 2006, 128, 14571-14578.
54. E. Napolitano, V. Farina, M. Persico, Organometallics 2003, 22, 4030-4037.
55. A. Ariafard, Z. Lin, I. J. S. Fairlamb, Organometallics 2006, 25, 5788-5794.
56. V. Ananikov, D. G. Musaev, K. Morokuma, J. Am. Chem. Soc. 2002, 124, 2839-2852.
57. V. Ananikov, D. G. Musaev, K. Morokuma, Organometallics 2005, 24, 715-723.
58. S. A. Macgregor, G. W. Neave, C. Smith, Faraday Discuss. 2003, 124, 111-127.
59. E. Zuidema, P. W. N. M. van Leeuwen, C. Bo, Organometallics 2005, 24, 3703-3710.
60. A. L. Casado, P. Espinet, Organometallics 1998, 17, 954-959.