Palladium-Catalyzed Annulation of Allenes Using Functionally Substituted Vinylic Halides

Journal of Organic Chemistry

Volumn 63, Issue 7, 1998, Pages 2154-2160

  Larock, R C ^a   He, Y ^a   Leong, W W ^a   Han, X ^a   Refvik, M D ^a   Zenner, J M ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000086173     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9717245     Document Type: Article

References (76)

1. (a) Trost, B. M. Tetrahedron 1977, 33, 2615.
2. (b) Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press: New York, 1982; Vol. 8, p 799.
3. (c) Tsuji, J. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: New York, 1985; Vol. 3, p 163.
4. (d) Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmel-hack, M. F., Eds.; Pergamon Press: New York, 1991; Vol. 4, p 585.
5. (e) Hegedus, L. S. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: New York, 1985; Vol. 2, p 401.
6. (f) Pearson, A. J. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: New York, 1985; Vol. 4, p 889.
7. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173.
8. (h) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
9. (a) Hughes, R. P.; Powell, J. J. Organomet. Chem. 1973, 60, 409.
10. (b) Stevens, R. R.; Shier, G. D. J. Organomet. Chem. 1970, 21, 495.
11. (c) Ban, E.; Hughes, R.; Powell, J. J. Organomet. Chem. 1974, 69, 455.
12. (d) Hughes, R. P.; Powell, J. J. Organomet. Chem. 1972, 34, C51.
13. (e) Hughes, R. P.; Powell, J. J. Chem. Soc., Chem. Commun. 1971, 275.
14. (f) Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274.
15. (g) Medema, D.; van Helden, R.; Kohll, C. F. Inorg. Chim. Acta 1969, 3, 255.
16. (h) van'Helden, R.; Kohll, C. F.; Medema, D.; Verberg, G.; Jonkhoff, T. Recl. Trav. Chim. Pays-Bas 1968, 87, 961.
17. (i) Medema, D.; van Helden, R. Recl. Trav. Chim. Pays-Bas 1971, 90, 304, 324.
18. (j) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019.
19. (k) Trost, B.; Kottirsch, G. J. Am. Chem. Soc. 1990, 112, 2816.
20. (l) Ogawa, A.; Kawakami, J.; Sonoda, N.; Hirao, T. J. Org. Chem. 1996, 61, 4161 .
21. (a) Ahmar, M.; Cazes, B.: Goré, J. Tetrahedron Lett. 1984, 25, 4505.
22. (b) Ahmar, M.; Barieux, J.-J.; Cazes, B.; Goré, J. Tetrahedron 1987,43, 513.
23. (c) Friess, B.; Gazes, B.; Goré, J. Tetrahedron Lett. 1988, 29, 4089.
24. (d) Chaptal, N.; Colovbray-Gotteland, V.; Grandjean, C.; Cazes, B.; Gore, J. Tetrahedron Lett. 1991, 32, 1795.
25. (e) Kopola, N.; Friess, B.; Cazes, B.; Goré, J. Tetrahedron Lett. 1989, 30, 3963.
26. (f) Gauthier, V.; Cazes, B.; Gore, J. Tetrahedron Lett. 1991, 32, 915.
27. (g) Shimizu, I.; Tsuji, J. Chem. Lett. 1984, 233.
28. (h) Cazes, B. Pure Appl. Chem. 1990, 62, 1867.
29. (i) Cazes, B.; Colovray, V.; Goré, J. Tetrahedron Lett. 1988, 29, 627.
30. (j) Aniès, C.; Cazes, B.; Goré, J. J. Chem. Res., Synop. 1996, 116.
31. (k) Vicart, N.; Cazes, B.; Goré, J. Tetrahedron Lett. 1995, 36, 5015.
32. (a) Ahmar, M.; Cazes, B.; Goré, J. Tetrahedron 1987, 43, 3453.
33. (b) Ahmar, M.; Cazes, B.; Goré, J. Tetrahedron Lett. 1985, 26, 3795.
34. (c) Besson, L.; Bazin, J.; Goré, J.; Cazes, B. Tetrahedron Lett. 1994, 35, 2881.
35. (a) Alper, H.; Hartstock, F. W.; Despeyroux, B. J. J. Chem. Soc., Chem. Commun. 1984, 905.
36. (b) Lathbury, D.; Vernon, P.; Gallagher, T. Tetrahedron Lett. 1986, 27, 6009.
37. (c) Fox, D. N. A.; Gallagher, T. Tetrahedron 1990, 46, 4697.
38. (d) Fox, D. N. A.; Lathbury, D.; Mahon, M. F.; Molloy, K. C.; Gallagher, T. J. Am. Chem. Soc. 1991, 113, 2652.
39. (e) Prasad, J. S.; Liebeskind, L. S. Tetrahedron Lett. 1988, 29, 4260.
40. Larock, R. C.; Yum, E. K. Synlett 1990, 529.
41. (a) Larock, R. C.; Berrios-Peña, N. G.; Fried, C. A. J. Org. Chem. 1991, 56, 2615.
42. (b) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482.
43. (c) Ma, S.; Negishi, E. J. Org. Chem. 1994, 59, 4730.
44. (d) Ma, S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345.
45. (a) Larock, R. C.; Berrios-Peña, N. G.; Narayanan, K. J. Org. Chem. 1990, 55, 3447.
46. (b) Larock, R. C.; Fried, C. A. J. Am. Chem. Soc. 1990, 112, 5882.
47. (c) O'Connor, J. M.; Stallman, B. J.; Clark, W. G.; Shu, A. Y. L.; Spada, R. E.; Stevenson, T. M.; Dieck, H. A. J. Org. Chem. 1983, 48, 807.
48. (a) Maitlis, P. M. J. Organomet. Chem. 1980, 200, 161.
49. (b) Pfeffer, M. Red. Trav. Chim. Pays-Bas 1990, 109, 567.
50. (c) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.
51. (d) Wensbo, D.; Eriksson, A.; Jeschke, T.; Annby, U.; Gronowitz, S.; Cohen, L. A. Tetrahedron Lett. 1993, 34, 2823.
52. (e) Chen, C.; Lieberman, D. R.; Larsen, R. D.; Reamer, R. A.; Verhoeven, T. R.; Reider, P. J. Tetrahedron. Lett. 1994, 35, 6981.
53. (f) Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270.
54. (g) Larock, R. C.; Doty, M. J.; Cacchi, S. J. Org. Chem. 1993, 58, 4579.
55. (h) Wensbo, D.; Eriksson, A.; Jeschke, T.; Annby, U.; Gronowitz, S.; Cohen, L. A. Tetrahedron Lett. 1993, 34, 6471.
56. (i) Smith, D. W.; Youcca, F. D.; Yevich, J. P.; Mattson, R. J.; Williams, A.; Ruediger, E. H.; Combrink, K. D., Pearce, B. C. European Patent 0 548 813 A1, 1993.
57. Binger, P.; Schuchardt, U. Chem. Ber. 1980, 113, 1063.
58. Piers, E.; Marais, P. C. J. Org. Chem. 1990, 55, 3454.
59. Hartley, F. R. Chem. Rev. 1969, 69, 799.
60. Nilsson, Y. I. M.; Andersson, P. G.; Bäckvall, J.-E. J. Am. Chem. Soc. 1993, 115, 6609.
61. Brandsma, L. In Synthesis of Acetylenes, Allenes, and Cumulenes: a Laboratory Manual; Elsevier Scientific Pub. Co.: New York, 1981; p 191.
62. (a)Landor, P. D. The Chemistry of Allenes; Academic Press: New York, 1982; Vol. 3, p 867.
63. (b) Skattebol, L. Acta Chem. Scand. 1963, 17, 1683.
64. Hoff, S.; Brandsma, L.; Arens, J. F. Red. Trav. Chim. Pays-Bas 1968, 87, 916.
65. Duboudin, J. G.; Jousseaume, B. J. Organomet. Chem. 1979, 168, 1.
66. (a) Denmark, S. E.; Jones, T. K. J. Org. Chem. 1982, 47, 4595.
67. (b) Marshall, J. A.; Shearer, B. G.; Crooks, S. L. J. Org. Chem. 1987, 52, 1236.
68. Marshall, J. A.; Jenson, T. M. J. Org. Chem. 1984, 49, 1707.
69. Kamiya, N.; Chikami, Y.; Ishii, Y. Synlett 1990, 675.
70. Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203.
71. Kamiya, N.; Chikami, Y.; Ishii, Y. Synlett 1990, 675.
72. Coperet, C.; Sugihara, T.; Wu, G.; Shimoyama, I.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 3422.
73. Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, G. D.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709.
74. Ma, S.; Lu, X. J. Chem. Soc., Chem. Commun. 1990, 1643.
75. Abad, A.; Arnó, M.; Pedro, J. R.; Seoane, E. J. Chem. Soc., Perkin Trans, 1 1983, 2471.
76. Klausner, Y. S.; Bodansky, M. Synthesis 1972, 455.