A new palladium-catalyzed benzannulation of conjugated enynes

Journal of the American Chemical Society

Volumn 118, Issue 16, 1996, Pages 3970-3971

  Saito, Shinichi ^a   Salter, Matthew M ^a   Gevorgyan, Vladimir ^a   Tsuboya, Norie ^a   Tando, Kazushi ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029949373     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9600486     Document Type: Article

References (25)

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7. The reaction of 2-tert-butyl-1-buten-3-yne and 2-(trimethylsilyl)-1-buten-3-yne afforded corresponding cyclodimerized products in lower yields, together with inseparable linear oligomers.
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9. The structure and reactivity of the corresponding alkyne-Pt(0) complex are well established. See: Glanville, J. O.; Stewart, J. M.; Grim, S. O. J. Organomet. Chem. 1967, 7, P9-P10. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667-2673. Greaves, E. O.; Lock, C. J. L.; Maitlis, P. M. Can. J. Chem. 1968, 46, 3879-3891. Tripathy, P. B.; Renoe, B. W.; Adzamli, K.; Roundhill, d. M. J. Am. Chem. Soc. 1971, 93, 4406-4410. Chatt, J.; Rowe, G. A.; Williams, A. A. Proc. Chem. Soc. 1957, 208-209. Cook, C D.; Allen, A. D. Can. J. Chem. 1964, 42, 1603-1608.
10. The structure and reactivity of the corresponding alkyne-Pt(0) complex are well established. See: Glanville, J. O.; Stewart, J. M.; Grim, S. O. J. Organomet. Chem. 1967, 7, P9-P10. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667-2673. Greaves, E. O.; Lock, C. J. L.; Maitlis, P. M. Can. J. Chem. 1968, 46, 3879-3891. Tripathy, P. B.; Renoe, B. W.; Adzamli, K.; Roundhill, d. M. J. Am. Chem. Soc. 1971, 93, 4406-4410. Chatt, J.; Rowe, G. A.; Williams, A. A. Proc. Chem. Soc. 1957, 208-209. Cook, C D.; Allen, A. D. Can. J. Chem. 1964, 42, 1603-1608.
11. The structure and reactivity of the corresponding alkyne-Pt(0) complex are well established. See: Glanville, J. O.; Stewart, J. M.; Grim, S. O. J. Organomet. Chem. 1967, 7, P9-P10. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667-2673. Greaves, E. O.; Lock, C. J. L.; Maitlis, P. M. Can. J. Chem. 1968, 46, 3879-3891. Tripathy, P. B.; Renoe, B. W.; Adzamli, K.; Roundhill, d. M. J. Am. Chem. Soc. 1971, 93, 4406-4410. Chatt, J.; Rowe, G. A.; Williams, A. A. Proc. Chem. Soc. 1957, 208-209. Cook, C D.; Allen, A. D. Can. J. Chem. 1964, 42, 1603-1608.
12. The structure and reactivity of the corresponding alkyne-Pt(0) complex are well established. See: Glanville, J. O.; Stewart, J. M.; Grim, S. O. J. Organomet. Chem. 1967, 7, P9-P10. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667-2673. Greaves, E. O.; Lock, C. J. L.; Maitlis, P. M. Can. J. Chem. 1968, 46, 3879-3891. Tripathy, P. B.; Renoe, B. W.; Adzamli, K.; Roundhill, d. M. J. Am. Chem. Soc. 1971, 93, 4406-4410. Chatt, J.; Rowe, G. A.; Williams, A. A. Proc. Chem. Soc. 1957, 208-209. Cook, C D.; Allen, A. D. Can. J. Chem. 1964, 42, 1603-1608.
13. The structure and reactivity of the corresponding alkyne-Pt(0) complex are well established. See: Glanville, J. O.; Stewart, J. M.; Grim, S. O. J. Organomet. Chem. 1967, 7, P9-P10. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667-2673. Greaves, E. O.; Lock, C. J. L.; Maitlis, P. M. Can. J. Chem. 1968, 46, 3879-3891. Tripathy, P. B.; Renoe, B. W.; Adzamli, K.; Roundhill, d. M. J. Am. Chem. Soc. 1971, 93, 4406-4410. Chatt, J.; Rowe, G. A.; Williams, A. A. Proc. Chem. Soc. 1957, 208-209. Cook, C D.; Allen, A. D. Can. J. Chem. 1964, 42, 1603-1608.
14. The structure and reactivity of the corresponding alkyne-Pt(0) complex are well established. See: Glanville, J. O.; Stewart, J. M.; Grim, S. O. J. Organomet. Chem. 1967, 7, P9-P10. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667-2673. Greaves, E. O.; Lock, C. J. L.; Maitlis, P. M. Can. J. Chem. 1968, 46, 3879-3891. Tripathy, P. B.; Renoe, B. W.; Adzamli, K.; Roundhill, d. M. J. Am. Chem. Soc. 1971, 93, 4406-4410. Chatt, J.; Rowe, G. A.; Williams, A. A. Proc. Chem. Soc. 1957, 208-209. Cook, C D.; Allen, A. D. Can. J. Chem. 1964, 42, 1603-1608.
15. For examples of transition metal catalyzed [4 + 2] cycloadditions and Diels-Alder reactions, see: Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. Jolly, R. S.; Luedtke, G.; Sheehan, D ; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. Mach, K.; Antropiusová, Petrusová, L.; Turecek, F.; Hanus, V.; Sedmera, P.; Schraml, J. J. Organomet. Chem. 1985, 289, 331-339. tom Dieck. H.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. van Leeuwen, P. W. N. M.; Roobeek, C. F. Tetrahedron 1981, 50, 1973-1983.
16. For examples of transition metal catalyzed [4 + 2] cycloadditions and Diels-Alder reactions, see: Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. Jolly, R. S.; Luedtke, G.; Sheehan, D ; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. Mach, K.; Antropiusová, Petrusová, L.; Turecek, F.; Hanus, V.; Sedmera, P.; Schraml, J. J. Organomet. Chem. 1985, 289, 331-339. tom Dieck. H.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. van Leeuwen, P. W. N. M.; Roobeek, C. F. Tetrahedron 1981, 50, 1973-1983.
17. For examples of transition metal catalyzed [4 + 2] cycloadditions and Diels-Alder reactions, see: Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. Jolly, R. S.; Luedtke, G.; Sheehan, D ; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. Mach, K.; Antropiusová, Petrusová, L.; Turecek, F.; Hanus, V.; Sedmera, P.; Schraml, J. J. Organomet. Chem. 1985, 289, 331-339. tom Dieck. H.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. van Leeuwen, P. W. N. M.; Roobeek, C. F. Tetrahedron 1981, 50, 1973-1983.
18. For examples of transition metal catalyzed [4 + 2] cycloadditions and Diels-Alder reactions, see: Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. Jolly, R. S.; Luedtke, G.; Sheehan, D ; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. Mach, K.; Antropiusová, Petrusová, L.; Turecek, F.; Hanus, V.; Sedmera, P.; Schraml, J. J. Organomet. Chem. 1985, 289, 331-339. tom Dieck. H.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. van Leeuwen, P. W. N. M.; Roobeek, C. F. Tetrahedron 1981, 50, 1973-1983.
19. For examples of transition metal catalyzed [4 + 2] cycloadditions and Diels-Alder reactions, see: Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. Jolly, R. S.; Luedtke, G.; Sheehan, D ; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. Mach, K.; Antropiusová, Petrusová, L.; Turecek, F.; Hanus, V.; Sedmera, P.; Schraml, J. J. Organomet. Chem. 1985, 289, 331-339. tom Dieck. H.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. van Leeuwen, P. W. N. M.; Roobeek, C. F. Tetrahedron 1981, 50, 1973-1983.
20. For examples of transition metal catalyzed [4 + 2] cycloadditions and Diels-Alder reactions, see: Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. Jolly, R. S.; Luedtke, G.; Sheehan, D ; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. Mach, K.; Antropiusová, Petrusová, L.; Turecek, F.; Hanus, V.; Sedmera, P.; Schraml, J. J. Organomet. Chem. 1985, 289, 331-339. tom Dieck. H.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. van Leeuwen, P. W. N. M.; Roobeek, C. F. Tetrahedron 1981, 50, 1973-1983.
21. For examples of transition metal catalyzed [4 + 2] cycloadditions and Diels-Alder reactions, see: Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. Jolly, R. S.; Luedtke, G.; Sheehan, D ; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. Mach, K.; Antropiusová, Petrusová, L.; Turecek, F.; Hanus, V.; Sedmera, P.; Schraml, J. J. Organomet. Chem. 1985, 289, 331-339. tom Dieck. H.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. van Leeuwen, P. W. N. M.; Roobeek, C. F. Tetrahedron 1981, 50, 1973-1983.
22. For examples of transition metal catalyzed [4 + 2] cycloadditions and Diels-Alder reactions, see: Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. Jolly, R. S.; Luedtke, G.; Sheehan, D ; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. Mach, K.; Antropiusová, Petrusová, L.; Turecek, F.; Hanus, V.; Sedmera, P.; Schraml, J. J. Organomet. Chem. 1985, 289, 331-339. tom Dieck. H.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. van Leeuwen, P. W. N. M.; Roobeek, C. F. Tetrahedron 1981, 50, 1973-1983.
23. A referee has suggested another mechanism; hydridopalladation of enyne 1 would give a 4-pallado-2-R-diene, which then could carbopalladate the starting enyne to give a palladiohexatriene 7 as an intermediate, and then electrolytic closure of 7 and β-elimination would regenerate the PdH catalyst and provide the observed aromatic compound. equation presented
24. Klusener, P. A. A.; Kulik, W.; Brandsma, L. J. Org. Chem. 1987, 52, 5261-5266.
25. For a review of cyclophane chemistry, see: Fögtie, J. P. Cyclophane Chemistry; Wiley: Chichester, England, 1993.