Intramolecular 1,n palladium migrations in polycyclic aromatic hydrocarbons. Palladium(II) versus palladium(iv) mechanisms: A theoretical study

Organometallics

Volumn 25, Issue 13, 2006, Pages 3130-3142

  Mota, Antonio J ^a,b   Dedieu, Alain ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITY OF GRANADA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ENTHALPY; HYDROGEN; MOLECULAR DYNAMICS; PALLADIUM; PHASE TRANSITIONS;

ORGANIC TRANSFORMATIONS; PALLADIUM COMPLEXES; TRANSITION STATES;

POLYCYCLIC AROMATIC HYDROCARBONS;

EID: 33745742184     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om060128a     Document Type: Article

References (57)

1. For some recent references see: (a) Tsuji, J. Palladium Reagents and Catalysis: New Perspectives for the 21st Century; John Wiley & Sons: New York, 2004.
2. (b) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons: New York, 2002.
3. (c)See also chapters 5, 6, 8-10, 13, and 15 in: Metal-Catalyzed Cross-Coupling Reactions, 2002 ed; de Meijere A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 5, pp 2217-2317.
4. See also: (a) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 1365.
5. (b) Herrmann, W. A.; Öfele, K.; Preysing, D. v.; Schneider, S. K. J. Organomet. Chem. 2003, 687, 1229.
6. (c) Palladium Chemistry in 2003: Recent Developments, special issue (Volume 687) of J. Organomet. Chem.; Bertrand, G., Ed.
7. (d) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285.
8. (e) Tietze, L. F.; Ila, H.; Bell, H. P. Chem. Rev. 2004, 104, 3453.
9. Dupont, J.; Consort, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527.
10. Canty, A. J. Acc. Chem. Res. 1992, 25, 83.
11. Canty, A. J.; van Koten, G. Acc. Chem. Res. 1995, 28, 406.
12. Canty, A. J. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E. I., Ed.; Wiley: New York, 2002; Vol. 1, Chapter II.4, p 189.
13. Catellani, M. Synlett 2003, 298.
14. van Beizen, R.; Elsevier, C. J.; Dedieu, A.; Veldman, N.; Spek, A. L. Organometallics 2003, 22, 722.
15. Wang, L.; Pan, Y.; Jiang, X.; Hu, H. Tetrahedron Lett. 2000, 41, 725.
16. Karig, G.; Moon, M.-T.; Thasana, N.; Gallagher, T. Org. Lett. 2002, 4, 3115.
17. Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2002, 124, 14326.
18. Campo, M. A.; Huang, Q.; Yao, T.; Tian, Q.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 11506.
19. Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 7460.
20. Zhao, J.; Larock, R. C. Org. Lett. 2005, 7, 701.
21. Bour, C.; Suffert, J. Org. Lett. 2005, 7, 653.
22. For a few recent examples of tandem or cascade reactions that may involve Pd(IV) palladacycles, see for instance: (a) Catallani, M.; Frignani, F.; Rangoni, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 119.
23. (b) Catellani, M.; Pure Appl. Chem. 2002, 74, 63.
24. (c) Ref 6.
25. (d) Motti, E.; Mignozzi, A.; Catellani, M. J. Am. Chem. Soc. 2004, 126, 78.
26. (e) Motti, E.; Rossetti, M. Bocelli, G.; Catellani, M. J. Organomet. Chem. 2004, 689, 3741.
27. (f) Grigg, R.; Loganathan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479.
28. (g) Dyker, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1023.
29. (h) Dyker, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 103.
30. (i) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1699.
31. (j) Albrecht, K.; Reiser, O.; Weber, M.; Knieriem, B.; de Meijere, A. Tetrahedron 1994, 50, 383.
32. (k) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
33. (l) Huang, Q.; Campo, M. A., Yao, T.; Tian, Q.; Larock, R. C. J. Org. Chem. 2004, 69, 8251.
34. Mota, A. J.; Dedieu, A.; Bour, C.; Suffert, J. J. Am. Chem. Soc. 2005, 127, 7171.
35. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
36. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
37. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
38. Frisch, M. J.; et al. Gaussian 03, Revision B.04; Gaussian, Inc.: Pittsburgh, PA, 2003.
39. Couty, M.; Hall, M. B. J. Comput. Chem. 1996, 17, 1359.
40. Hay, P. J. J. Chem. Phys. 1985, 82, 299.
41. Bergner, A.; Dolg, M.; Küchle, W.; Stoll, H.; Preuss, H. Mol. Phys. 1993, 80, 1431.
42. Glukhovtsev, M.; Pross, A.; McGrath, M. P.; Radom, L. J. Chem. Phys. 1995, 103, 1878.
43. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
44. Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 16, 217.
45. Alcazar-Roman, L. M.; Hartwig, J. F.; Rheingold, A. L.; Liable-Sands, L. M.; Guzei, I. A. J. Am. Chem. Soc. 2000, 122, 4618.
46. Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043.
47. Stambuli, J. P.; Incarvito, C. D.; Bühl, M.; Hartwig, J. F: J. Am. Chem. Soc. 2004, 126, 1184.
48. Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373.
49. Stambuli, J. P.; Bühl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9346.
50. Galardon, E.; Ramdeehul, S.; Brown, J. M.; Cowley, A.; Hii, K. K.; Jutand, A. Angew. Chem. Int. Ed. 2002, 41, 1760.
51. Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.
52. Louie, J.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11598.
53. Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 13978.
54. Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 13178.
55. Note that whereas a trans-trans rearrangement can take place and is found to be more energy demanding than the cis-trans rearrangement, a cis-cis rearrangement is not possible; see the Supporting Information for the corresponding analysis.
56. Oxgaard, J.; Muller, R. P.; Goddard, W. A., III; Periana, R. A. J. Am. Chem. Soc. 2004, 126, 352.
57. Oxgaard, J.; Periana, R. A.; Goddard, W. A., III. J. Am. Chem. Soc. 2004, 126, 11658.