Palladium catalyzed intramolecular hydrocarbonation of allenes leading to carbocycles

Tetrahedron Letters

Volumn 37, Issue 41, 1996, Pages 7453-7456

  Meguro, Masaki ^a   Kamijo, Shin ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030574040     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01609-7     Document Type: Article

References (28)

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12. For 1,3-diene, see c) Takahashi, K.; Miyake, A.; Hata, G. Chem. Ind. (London) 1971, 488.; Takahashi, K.; Miyake, A.; Hata, G. Bull. Chem. Soc. Jpn. 1972, 45, 1183-1191.; Andell, O. S.; Bäckvall, J.-E. Moberg, C. Acta Chem. Scand. Ser. B 1986, 40, 184-189.; Jolly, P. W.; Kokel, N. Synthesis 1990, 771-773.; Mercier, C.; Mignani, G.; Aufrand, N.; Allmang, G. Tetrahedron Lett. 1991, 32, 1433-1436.; Trost, B. M.; Zhi, L. Tetrahedron Lett. 1992, 33, 1831-1834.
13. For 1,3-diene, see c) Takahashi, K.; Miyake, A.; Hata, G. Chem. Ind. (London) 1971, 488.; Takahashi, K.; Miyake, A.; Hata, G. Bull. Chem. Soc. Jpn. 1972, 45, 1183-1191.; Andell, O. S.; Bäckvall, J.-E. Moberg, C. Acta Chem. Scand. Ser. B 1986, 40, 184-189.; Jolly, P. W.; Kokel, N. Synthesis 1990, 771-773.; Mercier, C.; Mignani, G.; Aufrand, N.; Allmang, G. Tetrahedron Lett. 1991, 32, 1433-1436.; Trost, B. M.; Zhi, L. Tetrahedron Lett. 1992, 33, 1831-1834.
14. For 1,3-diene, see c) Takahashi, K.; Miyake, A.; Hata, G. Chem. Ind. (London) 1971, 488.; Takahashi, K.; Miyake, A.; Hata, G. Bull. Chem. Soc. Jpn. 1972, 45, 1183-1191.; Andell, O. S.; Bäckvall, J.-E. Moberg, C. Acta Chem. Scand. Ser. B 1986, 40, 184-189.; Jolly, P. W.; Kokel, N. Synthesis 1990, 771-773.; Mercier, C.; Mignani, G.; Aufrand, N.; Allmang, G. Tetrahedron Lett. 1991, 32, 1433-1436.; Trost, B. M.; Zhi, L. Tetrahedron Lett. 1992, 33, 1831-1834.
15. For 1,3-diene, see c) Takahashi, K.; Miyake, A.; Hata, G. Chem. Ind. (London) 1971, 488.; Takahashi, K.; Miyake, A.; Hata, G. Bull. Chem. Soc. Jpn. 1972, 45, 1183-1191.; Andell, O. S.; Bäckvall, J.-E. Moberg, C. Acta Chem. Scand. Ser. B 1986, 40, 184-189.; Jolly, P. W.; Kokel, N. Synthesis 1990, 771-773.; Mercier, C.; Mignani, G.; Aufrand, N.; Allmang, G. Tetrahedron Lett. 1991, 32, 1433-1436.; Trost, B. M.; Zhi, L. Tetrahedron Lett. 1992, 33, 1831-1834.
16. For 1,3-diene, see c) Takahashi, K.; Miyake, A.; Hata, G. Chem. Ind. (London) 1971, 488.; Takahashi, K.; Miyake, A.; Hata, G. Bull. Chem. Soc. Jpn. 1972, 45, 1183-1191.; Andell, O. S.; Bäckvall, J.-E. Moberg, C. Acta Chem. Scand. Ser. B 1986, 40, 184-189.; Jolly, P. W.; Kokel, N. Synthesis 1990, 771-773.; Mercier, C.; Mignani, G.; Aufrand, N.; Allmang, G. Tetrahedron Lett. 1991, 32, 1433-1436.; Trost, B. M.; Zhi, L. Tetrahedron Lett. 1992, 33, 1831-1834.
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23. 5. For a direct addition of an aromatic H-C bond to a double bond, see Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kametani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529-531. and references cited therein.
24. 3P were not effective as a catalyst.
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26. 8. Kündig, K. P.; Cunningham, Jr., A. F. Tetrahedron 1988, 44, 6855-6860.
27. 9. Several transition metal complexes of pronucleophiles have been reported. For Re, see Hirao, M.; Ito, Y.; Hirai, M.; Fukuoka, A.; Komiya, S. Chem. Lett. 1993, 2057-2067.; For Ru, see Murahashi, S.-I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436-12451.; We also confirmed a rapid C-H insertion of Pd(0) into methylmalononitrile. See ref. 4a.
28. 9. Several transition metal complexes of pronucleophiles have been reported. For Re, see Hirao, M.; Ito, Y.; Hirai, M.; Fukuoka, A.; Komiya, S. Chem. Lett. 1993, 2057-2067.; For Ru, see Murahashi, S.-I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436-12451.; We also confirmed a rapid C-H insertion of Pd(0) into methylmalononitrile. See ref. 4a.