Reactions of free radicals with η3-allylpalladium(II) complexes: Phenyl and trityl radicals

Journal of the Chemical Society. Dalton Transactions

Volumn , Issue 20, 2003, Pages 3975-3980

  Reid, Simon J ^a   Baird, Michael C ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; FREE RADICALS; ISOMERIZATION; PYROLYSIS; REACTION KINETICS; UNSATURATED COMPOUNDS;

ALLYLPALLADIUM COMPLEXES; PHENYL RADICALS; TRITYL RADICALS;

PALLADIUM COMPOUNDS;

EID: 0142227766     PISSN: 14779226     EISSN: None     Source Type: Journal    
DOI: 10.1039/B307308D     Document Type: Article

References (69)

1. (a) D. P. Curran, in Comprehensive Organic Synthesis, Pergamon Press, New York, 1991, vol. 4, p. 715
2. (b) B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press, Oxford, 1986
3. (c) D. P. Curran, N. A. Porter and B. Giese, Stereochemistry of Radical Reactions, VCH, Weinhem, 1996
4. (d) J. A. M. Simoes, A. Greenberg and J. F. Liebman, Energetics of Organic Free Radicals, Blackie Academic and Professionals, 1996
5. (e) J. E. Leffler, An Introduction to Free Radicals, John Wiley and Sons, New York, 1993
6. (f) H. Fischer and L. Radom, Angew. Chem., Int. Ed., 2001, 40, 1340.
7. J. K. Stille, in The Chemistry of the Metal-Carbon Bond, ed. F. R. Hartley and S. Patai, Wiley and Sons, Chichester, 1985, vol. 2, ch. 9
8. (b) L. M. Rendina and R. J. Puddephatt, Chem. Rev., 1997, 97, 1735.
9. A. Krief and A. M. Laval, Chem. Rev., 1999, 99, 745.
10. (a) J. K. Kochi and J. W. Powers, J. Am. Chem. Soc., 1970, 92, 137
11. (b) R. Sustmann and R. Altevogt, Tetrahedron Lett., 1981, 22, 5167.
12. (a) R. L. Sweaney, D. S. Comberrel, M. D. Dombourian and N. A. Peters, J. Organomet. Chem., 1981, 216, 57
13. (b) F. Ungváry and L. Markó, Organometallics, 1982, 1, 1120
14. (c) T. M. Bockman, J. F. Garst, R. B. King, L. Markó and F. Ungváry, J. Organomet. Chem, 1985, 279, 165
15. (d) R. M. Bullocko and E. G. Samsel, J. Am. Chem. Soc., 1990, 112, 6886.
16. (a) J. W. Connolly, Organometallics, 1984, 3, 1333
17. (b) F. Ungváry and L. Markó, Organometallics, 1984, 3, 1466
18. (c) B. Wassink, M. J. Thomas, S. C. Wright, D. J. Gillis and M. C. Baird, J. Am. Chem. Soc., 1987, 109, 1995
19. (d) T. A. Shackleton, S. C. Mackie, S. B. Fergusson, L. J. Johnston and M. C. Baird, Organometallics, 1990, 9, 2248.
20. (a) E. Baciocchi, B. Floris and E. Muraglia, J. Org. Chem., 1993, 58, 2013
21. (b) H.-G. Schmalz, S. Siegel and J. W. Bats, Angew. Chem., Int. Ed. Engl., 1995, 34, 2383
22. (c) H.-G. Schmalz, S. Siegel and A. Schwarz, Tetrahedron Lett., 1996, 17, 2947.
23. (a) C. A. G. Carter, R. McDonald and J. M. Stryker, Organometallics, 1999, 18, 820
24. (b) S. Ogoshi and J. M. Stryker, J. Am. Chem. Soc., 1998, 120, 3514
25. (c) G. L. Casty and J. M. Stryker, J. Am. Chem. Soc., 1995, 117, 7814.
26. C. A. Merlic and D. Xu, J. Am. Chem. Soc., 1991, 113, 9855.
27. G. G. Melikyan, O. Vostrowsky, W. Bauer, H. J. Bestmann, M. Khan and K. M. Nicholas, J. Org. Chem., 1994, 59, 222.
28. K. E. Torraca and L. McElwee-White, Coord. Chem. Rev., 2000, 206-207, 469.
29. (a) S. A. Godleski, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 4, p. 585
30. (b) F. Guibe, Tetrahedron, 1998, 54, 2967
31. (c) J. Tsuji, Palladium Reagents and Catalysis: Innovations in Organic Synthesis, Wiley, Chichester, 1995
32. (d) P. J. Harrington, Comprehensive Organometallic Chemistry, II, vol. 12 (ed. E. W. Abel, F. G. A. Stone and G. Wiljkinson, Elsevier, New York, 1995, p. 797.
33. (a) S. G. Cohen and C. H. Wang, J. Am. Chem. Soc., 1953, 75, 5504
34. (b) R. R. Bridger and G. A. Russell, J. Am. Chem. Soc., 1963, 85, 3754
35. (c) R. G. Kryger, J. P. Lorand, N. R. Stevens and N. R. Herron, J. Am. Chem. Soc., 1977, 99, 7589.
36. T. H. Colle, P. S. Glaspie and E. S. Lewis, J. Org. Chem., 1978, 43, 2722.
37. S. J. Reid, N. T. Freeman and M. C. Baird, Chem. Commun., 2000, 1777.
38. D. R. Coulson, Inorg. Synth., 1972, 13, 121.
39. V. V. Grushin, C. Bensimon and H. Alper, Organometallics, 1995, 14, 3259.
40. (a) W. T. Dent, R. Long and A. J. Wilkinson, J. Chem. Soc., 1964, 1585
41. (b) M. Sakakibara, Y. Takahashi, S. Sakai and Y. Ishii, Chem. Commun., 1969, 396
42. (c) G. L. Statton and K. C. Ramey, J. Am. Chem. Soc., 1966, 88, 1327
43. (d) K. C. Ramey and G. L. Statton, J. Am. Chem. Soc., 1966, 88, 4837.
44. J.-E. Bäckvall, R. E. Nordberg, K. Zetterberg and B. Åkermark, Organometallics, 1989, 2, 1625.
45. H. C. Volger and K. Vrieze, J. Organomet. Chem., 1967, 9, 527.
46. (a) D. R. Coulson, Chem. Commun., 1968, 1530
47. (b) P. Fitton, M. P. Johnson and J. E. McKeon, Chem. Commun., 1968, 6
48. (c) A. Mentes, R. D. W. Kemmitt, J. Fawcett and D. R. Russeli, Polyhedron, 1999, 18, 1141.
49. (a) E. Moret, F. Fürrer and M. Schlosser, Tetrahedron, 1988, 44, 3539
50. (b) J.-P. Dau-Schmidt and H. Mayr, Chem. Ber., 1994, 127, 205
51. (c) K. Nozaki, T. Nanno and J. Takaya, J. Organomet. Chem., 1997, 527, 103.
52. V. V. Grushin, Organometallics, 2000, 19, 1888.
53. (a) A. Sonoda, B. E. Mann and P. M. Maitlis, J. Chem. Soc., Chem. Commun., 1975, 108
54. (b) B. E. Mann, A. Keasey, A. Sonoda and P. M. Maitlis, J. Chem. Soc., Dalton Trans., 1979, 338
55. (c) A. Sonoda, P. M. Bailey and P. M. Maitlis, J. Chem. Soc., Dalton Trans., 1979, 346
56. (d) S. J. Reid and M. C. Baird, Organometallics, 1997, 16, 2481.
57. (a) B. Crociani, S. Antonaroli, F. Di Bianca and A. Fontana, J. Organomet. Chem., 1993, 450, 21
58. (b) B. M. Trost and T. R. Verhoeven, J. Am. Chem. Soc., 1980, 102, 4730
59. (c) H. Kurosawa, H. Kajimaru, S. Ogoshi, H. Yoneda, K. Miki, N. Kasai, S. Murai and I. Ikeda, J. Am. Chem. Soc., 1992, 114, 8417.
60. (a) G. K. Anderson, H. C. Clark and J. A. Davies, Organometallics, 1982, 1, 64
61. (b) C. Eaborn, K. J. Odell and A. Pidcock, J. Chem. Soc., Dalton Trans., 1978, 357
62. (c) C. Eaborn, A. Pidcock and B. R. Steele, J. Chem. Soc., Dalton Trans., 1976, 767
63. (d) M. C. Baird and G. Wilkinson, J. Chem. Soc. A, 1967, 865
64. (e) M. A. Baird, J. Inorg. Nucl. Chem., 1967, 29, 367.
65. M. C. Baird, Chem. Rev., 1988, 88, 1217.
66. M. C. Baird, J. Organomet. Chem., 1974, 64, 289.
67. (a) I. I. Moiseev, T. A. Stromnova and M.N. Vargaftik J. Mol. Catal., 1994, 86, 71
68. (b) R. Touroude, L. Hilaire and F. G. Gault J. Catal., 1974, 32, 279
69. (c) N. R. Davies, Aust. J. Chem., 1964, 17, 212.