Palladium-catalyzed benzannulation of conjugated enynes. Enhanced reactivity of alkoxycarbonyl- and cyanoenynes

Tetrahedron Letters

Volumn 40, Issue 42, 1999, Pages 7529-7532

  Saito, Shinichi ^a   Tsuboya, Norie ^a   Chounan, Yukiyasu ^b   Nogami, Tsutomu ^b   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b HIROSAKI UNIVERSITY   (Japan)

Author keywords

Cycloadditions; Enynes; Palladium and compounds

Indexed keywords

ALKYNE DERIVATIVE; BENZENE DERIVATIVE; CYANIC ACID DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CYCLIZATION; STEREOCHEMISTRY;

EID: 0033570257     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01520-8     Document Type: Article

References (9)

1. Saito, S.; Salter, M. M.; Gevorgyan, V.; Tsuboya, N.; Tando, K.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 3970-3971.
2. Gevorgyan, V.; Tando, K.; Uchiyama, N.; Yamamoto, Y. J. Org. Chem. 1998, 63, 7022-7025.
3. These conjugated enynes also reacted with conjugated diynes in the presence of palladium catalysts to give benzene derivatives. See: (a) Gevorgyan, V.; Takeda, A.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 11313-11314. (b) Gevorgyan, V.; Sadayori, N.; Yamamoto, Y. Tetrahedron Lett. 1997, 38, 8603-8604.
4. These conjugated enynes also reacted with conjugated diynes in the presence of palladium catalysts to give benzene derivatives. See: (a) Gevorgyan, V.; Takeda, A.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 11313-11314. (b) Gevorgyan, V.; Sadayori, N.; Yamamoto, Y. Tetrahedron Lett. 1997, 38, 8603-8604.
5. (a) Saito, S.; Tsuboya, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 5042-5047. (b) Weibel, D.; Gevorgyan, V.; Yamamoto, Y. J. Org. Chem. 1998, 63, 1217-1220. (c) Gevorgyan, V.; Quan, L.-G.; Yamamoto, Y. J. Org. Chem. 1998, 63, 1244-1247.
6. (a) Saito, S.; Tsuboya, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 5042-5047. (b) Weibel, D.; Gevorgyan, V.; Yamamoto, Y. J. Org. Chem. 1998, 63, 1217-1220. (c) Gevorgyan, V.; Quan, L.-G.; Yamamoto, Y. J. Org. Chem. 1998, 63, 1244-1247.
7. (a) Saito, S.; Tsuboya, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 5042-5047. (b) Weibel, D.; Gevorgyan, V.; Yamamoto, Y. J. Org. Chem. 1998, 63, 1217-1220. (c) Gevorgyan, V.; Quan, L.-G.; Yamamoto, Y. J. Org. Chem. 1998, 63, 1244-1247.
8. The enhanced reactivity of alkoxycarbonylenynes in the cross benzannulation was reported. See Ref. 3b.
9. On the other hand, higher temperature (65°C or 100°C) were required for the reaction of 2-alkylenynes or 4-alkylenynes. See Refs. 1 and 2.