DFT computational study of the mechanism of allyl halides carbonylation catalyzed by nickel tetracarbonyl

Journal of the American Chemical Society

Volumn 125, Issue 34, 2003, Pages 10412-10419

  Bottoni, Andrea ^a   Miscione, Gian Pietro ^a   Novoa, Juan J ^b   Prat Resina, Xavier ^c  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF BARCELONA   (Spain)

^c UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; COMPLEXATION; COMPUTATIONAL METHODS; NICKEL COMPOUNDS; OXIDATION;

CATALYTIC CYCLE;

CARBONYLATION;

BROMIDE; HALIDE; NICKEL COMPLEX; NICKEL TETRACARBONYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; MATHEMATICAL ANALYSIS; OXIDATION; REACTION ANALYSIS; REDUCTION; THEORY;

EID: 84961983823     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030100f     Document Type: Article

References (45)

1. Beller, M.; Cornilis. B.; Frohning, C. D.; Kohlpaintner, C. W. J. Mol. Catal. 1995, 104, 17.
2. Chiusoli, G. P. Chim. Ind. 1959, 41, 503.
3. Tsuji, J.; Morikawa, M.; Kiji, J. Tetrrahedron Lett. 1963, 1811.
4. Joo, F.; Alper, H. Organometallics 1985, 4, 1775. Murahashi, S.-I.; Imada, Y.; Taniguchi, Y.; Higashiura, S. Tetrrahedron Lett. 1988, 29, 4945.
5. Joo, F.; Alper, H. Organometallics 1985, 4, 1775. Murahashi, S.-I.; Imada, Y.; Taniguchi, Y.; Higashiura, S. Tetrrahedron Lett. 1988, 29, 4945.
6. Yamamoto, A. Bull. Chem. Soc. Jpn. 1995, 68, 433.
7. Jiang, H.; Xu, Y.; Liao, S.; Yu, D.; Chen, H.; Li, X. J. Mol. Catal. A: Chemical 1998, 130, 79.
8. Bertoux, F.; Monflier, E.; Castanet, Y.; Mortreux, A. J. Mol. Catal. A: Chemical 1999, 143, 11.
9. Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Woodall, D. E.; Yoganathan, G. Tetrrahedron Lett. 2000, 41, 7125.
10. Bio, M. M.; Leighton, L. Organic Lett. 2000, 2, 2905.
11. El. Houssame, S.; El. Firdoussi, L.; Allaoud, S.; Karim, A. Castanet, Y. ; Mortreux, A. J. Mol. Catal. A: Chemical 2001, 168, 15.
12. Chiusoli, G. P. Angew. Chem. 1960, 72, 74.
13. Heck, R. F. J. Am. Chem. Soc. 1963, 85, 2013.
14. Chiusoli, G. P.; Cassar, L. Angew. Chem., Int. Ed. Engl. 1967, 6, 124.
15. Heck, R. F. Acc. Chem. Res. 1969, 2, 10.
16. Chiusoli, G. P. Acc. Chem. Res. 1973, 6, 422.
17. Kuhlmann, E. J.; Alexander, J. J. Coord. Chem. Rev. 1980, 33, 195.
18. Camps, F.; Coll, J.; Moreto, J. M.; Torras, J. J. Org. Chem. 1989, 54, 1969.
19. Pages, L.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moreto, J. M. J. Am. Chem. Soc. 1992, 114, 10 449.
20. Garcia-Gomez, G.; Moreto, J. M. J. Am. Chem. Soc. 1999, 121, 878.
21. Bernardi, F.; Bottoni, A.; Nicastro, M.; Rossi, I.; Novoa, J.; Prat, X. Organometallics 2000, 19, 2170.
22. Day, J. P.; Pearson, R. G.; Basolo, F. J. Am. Chem. Soc. 1968, 90, 6933.
23. Cotton, Ficher, Wilkinson, J. Am. Chem. Soc. 1959, 81, 100.
24. Johnson, J. R.; Tully, P. S.; Mackenzie, P. B.; Sabat, M. J. Am. Chem. Soc., 1991, 113, 6172.
25. Grisso, B. A.; Johnson, J. R.; Mackenzie, P. B. J. Am. Chem. Soc. 1992, 114, 5160.
26. De Angelis, F.; Re, N.; Sgamellotti, A.; Selloni, A.; Weber, J.; Floriani, C. Chem. Phys. Lett. 1998, 291, 57.
27. De Angelis, F.; Sgamellotti. A. Organometallics 2000, 19, 4104.
28. Carbo, J. J.; Bo, C.; Poblet, J. M.; Moreto, J. M. Organometallics 2000, 19, 3516.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.;Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA. 1998.
30. Becke, A. D. J. Chem. Phys. 1993. 98, 1372, 5648.
31. Stephens, P. J.; Devlin, F. J.; Chabalowsky, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11 623.
32. Hohenberg, P.; Kohn, W. Phys. Rev. B 1964, 136, 864. Kohn, W.; Sham, L. J. Phys. Rev. A 1965, 140, 1133.
33. Hohenberg, P.; Kohn, W. Phys. Rev. B 1964, 136, 864. Kohn, W.; Sham, L. J. Phys. Rev. A 1965, 140, 1133.
34. Becke, A. D. Phys. Rev. 1988, A38, 3098.
35. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
36. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785.
37. Miehlich, A.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
38. Bernardi, F.; Bottoni, A.; Miscione, G. P. J. Am. Chem. Soc. 1997, 119, 12 300.
39. Bernardi, N.; Bottoni, A.; Casolari, S.; Tagliavini, E. J. Org. Chem. 2000, 65, 4783.
40. Bottoni, A.; Perez Higueruelo, A.; Miscione, G. P. J. Am. Chem. Soc. 2002, 124, 5506.
41. Bernardi, F.; Bottoni, A.; Garavelli, M. Quant. Struct.-Act. Relat. 2002, 21, 128.
42. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560. UniChem DGauss, Version 2.3.1, 1994, Cray Research, Inc.
43. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560. UniChem DGauss, Version 2.3.1, 1994, Cray Research, Inc.
44. Miertus, S.; Scrocco, E.; Tomasi, J. J. Chem. Phys. 1981, 55, 117. Miertus, S.; Tomasi, J. J. Chem. Phys. 1982, 65, 239.
45. Miertus, S.; Scrocco, E.; Tomasi, J. J. Chem. Phys. 1981, 55, 117. Miertus, S.; Tomasi, J. J. Chem. Phys. 1982, 65, 239.