Palladium-catalyzed electrophilic allylation reactions via bis(allyl)palladium complexes and related intermediates

Chemistry - A European Journal

Volumn 10, Issue 21, 2004, Pages 5268-5275

  Szabó, Kálmán J ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Allylation; Density functional calculations; Electrophilic substitution; Homogeneous catalysis; Palladium

Indexed keywords

ALDEHYDES; CATALYSTS; PALLADIUM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ELECTROPHILES; ELECTROPHILIC ALLYLATION REACTIONS; ELECTROPHILIC REAGENTS;

CATALYSIS;

ALDEHYDE; ALLYL COMPOUND; BIS(ALLYL)PALLADIUM COMPLEX; IMINE; PALLADIUM; PALLADIUM COMPLEX; REAGENT; UNCLASSIFIED DRUG;

ALLYLATION; CATALYSIS; CATALYST; DENSITY FUNCTIONAL THEORY; MICHAEL ADDITION; REVIEW; SUBSTITUTION REACTION; SYNTHESIS;

EID: 8344265265     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400261     Document Type: Review

References (53)

1. J. Tsuji, Perspectives in Organopalladium Chemistry for the 21st Century, Elsevier, Amsterdam, 1999.
2. J. Tsuji, Palladium Reagents and Catalysis: Innovations in Organic Synthesis, Wiley, Chichester, 1995.
3. E. Negishi, A. de Meijre, Organopalladium Chemistry for Organic Synthesis, Vol. 2, Wiley, New York, 2002.
4. H. Nakamura, H. Iwama, Y. Yamamoto, J. Am. Chem. Soc. 1996, 118, 6641.
5. H. Nakamura, H. Iwama, Y. Yamamoto, Chem. Commun. 1996, 1459.
6. H. Nakamura, J.-G. Shim, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8113.
7. H. Nakamura, K. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 4242.
8. E. Yoshikawa, K. V. Radhakrishnan, Y. Yamamoto, Tetrahedron Lett. 2000, 41, 729.
9. H. Nakamura, K. Aoyagi, J.-G. Shim, Y. Yamamoto, J. Am. Chem. Soc. 2001, 123, 372.
10. H. Nakamura, M. Bao, Y. Yamamoto, Angew. Chem. 2001, 113, 3308; Angew. Chem. Int. Ed. 2001, 40, 3208.
11. H. Nakamura, M. Bao, Y. Yamamoto, Angew. Chem. 2001, 113, 3308; Angew. Chem. Int. Ed. 2001, 40, 3208.
12. R. A. Fernandes, A. Stimac, Y. Yamamoto, J. Am. Chem. Soc. 2003, 125, 14133.
13. K. J. Szabó, Chem. Eur. J. 2000, 6, 4413.
14. N. Solin, S. Narayan, K. J. Szabó, J. Org. Chem. 2001, 66, 1686.
15. N. Solin, S. Narayan, K. J. Szabó, Org. Lett. 2001, 3, 909.
16. O. A. Wallner, K. J. Szabó, Org. Lett. 2002, 4, 1563.
17. O. A. Wallner, K. J. Szabó, J. Org. Chem. 2003, 68, 2934.
18. O. A. Wallner, K. J. Szabó, Chem. Eur. J. 2003, 9, 4025.
19. N. Solin, J. Kjellgren, K. J. Szabó, Angew. Chem. 2003, 115, 3784; Angew. Chem. Int. Ed. 2003, 42, 3656.
20. N. Solin, J. Kjellgren, K. J. Szabó, Angew. Chem. 2003, 115, 3784; Angew. Chem. Int. Ed. 2003, 42, 3656.
21. B. M. Trost, Acc. Chem. Res. 1980, 13, 385.
22. S. A. Godleski, in Nucleophiles with Allyl-Metal Complexes, Vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, Chapter 3.3.
23. B. M. Trost, D. L. V. Vranken, Chem. Rev. 1996, 96, 395.
24. B. M. Trost, Acc. Chem. Res. 1996, 29, 355.
25. J. Tsuji, T. Mandai, Angew. Chem. 1995, 107, 2830; Angew. Chem. Int. Ed. Engl. 1995, 34, 2589.
26. J. Tsuji, T. Mandai, Angew. Chem. 1995, 107, 2830; Angew. Chem. Int. Ed. Engl. 1995, 34, 2589.
27. B. Henc, P. W. Jolly, R. Salz, G. Wilke, R. Benn, E. G. Hoffmann, R. Mynott, G. Schroth, K. Seevolgel, J. C. Sekutowski, C. Krüger, J. Organomet. Chem. 1980, 191, 425.
28. A. Goliaszewski, J. Schwartz, J. Am. Chem. Soc. 1984, 106, 5028.
29. A. Goliaszewski, J. Schwartz, Tetrahedron 1985, 41, 5779.
30. J. E. Gozum, D. M. Pollina, J. A. Jensen, G. S. Girolami, J. Am. Chem. Soc. 1988, 110, 2688.
31. P. W. Jolly, Angew. Chem. 1985, 97, 279; Angew. Chem. Int. Ed. Engl. 1985, 24, 283.
32. P. W. Jolly, Angew. Chem. 1985, 97, 279; Angew. Chem. Int. Ed. Engl. 1985, 24, 283.
33. J. Krause, R. Goddard, R. Mynott, K.-R. Pörschke, Organometallics 2001, 20, 1992.
34. R. Benn, P.W. Jolly, R. Mynott, B. Raspel, G. Schenker, K.-P. Schick, G. Schrot, Organometallics 1985, 4, 1945.
35. K. J. Szabó, Organometallics 1996, 15, 1128.
36. M. Méndez, J. M. Cuerva, E. Gómez-Bengoa, D. J. Cárdenas, A. M. Echavarren, Chem. Eur. J. 2002, 8, 3620.
37. The B3PW91 complexation energy originally published in ref. [12] was overestimated because of basis set related errors.
38. E. J. Smutny, J. Am. Chem. Soc. 1967, 89, 6793.
39. S. Takahashi, T. Shibano, N. Hagihara, Tetrahedron Lett. 1967, 8, 2451.
40. A. Zapf, M. Beller, Top. Catal. 2002, 19, 101.
41. R. Jackstell, M. G. Andreu, A. Frisch, K. Selvakumar, A. Zapf, H. Klein, A. Spannenberg, D. Röttger, O. Briel, R. Karch, M. Beller, Angew. Chem. 2002, 114, 1028; Angew. Chem. Int. Ed. 2002, 41, 986.
42. R. Jackstell, M. G. Andreu, A. Frisch, K. Selvakumar, A. Zapf, H. Klein, A. Spannenberg, D. Röttger, O. Briel, R. Karch, M. Beller, Angew. Chem. 2002, 114, 1028; Angew. Chem. Int. Ed. 2002, 41, 986.
43. T. Prinz, B. Driessen-Hölscher, Chem. Eur. J. 1999, 5, 2069.
44. M. S. Viciu, F. K. Zinn, E. D. Stevens, S. P. Nolan, Organometallics 2003, 22, 3175.
45. R. J. Franks, K. M. Nicholas, Organometallics 2000, 19, 1458.
46. N. Solin, K. J. Szabó, Organometallics 2001, 20, 5464.
47. H. Kurosawa, A. Urabe, Chem. Lett. 1985, 1839.
48. H. Kurosawa, A. Urabe, K. Miki, N. Kasai, Organometallics 1986, 5, 2002.
49. M. Albrecht, G. v. Koten, Angew. Chem. 2001, 113, 3866; Angew. Chem. Int. Ed. 2001, 40, 3750.
50. M. Albrecht, G. v. Koten, Angew. Chem. 2001, 113, 3866; Angew. Chem. Int. Ed. 2001, 40, 3750.
51. H. Rimml, L. M. Venanzi, J. Organomet. Chem. 1983, 259, C6.
52. R. B. Bedford, S. M. Draper, P. N. Scully, S. L. Welch, New J. Chem. 2000, 24, 745.
53. N. Solin, J. Kjellgren, K. J. Szabó, J. Am. Chem. Soc. 2004, 126, 7026.