Intramolecular nucleophilic addition of aryl bromides to ketones catalyzed by palladium

Journal of the American Chemical Society

Volumn 122, Issue 19, 2000, Pages 4827-4828

  Quan, Long Guo ^a   Lamrani, Mouad ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BROMIDE; HEXANOL; KETONE; N,N DIMETHYLFORMAMIDE; PALLADIUM; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; ELECTROCHEMICAL ANALYSIS; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0000379185     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000415k     Document Type: Article

References (15)

1. For reviews, see for example: (a) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, p 799. (b) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1978. (c) Tsuji, J. Palladium Reagents and Catalysts; John Wiley: Chiester, 1995. (d) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.- Y.; Liu, F. Chem. Rev. 1996, 96, 365.
2. For reviews, see for example: (a) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, p 799. (b) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1978. (c) Tsuji, J. Palladium Reagents and Catalysts; John Wiley: Chiester, 1995. (d) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.- Y.; Liu, F. Chem. Rev. 1996, 96, 365.
3. For reviews, see for example: (a) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, p 799. (b) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1978. (c) Tsuji, J. Palladium Reagents and Catalysts; John Wiley: Chiester, 1995. (d) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.- Y.; Liu, F. Chem. Rev. 1996, 96, 365.
4. For reviews, see for example: (a) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, p 799. (b) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1978. (c) Tsuji, J. Palladium Reagents and Catalysts; John Wiley: Chiester, 1995. (d) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365.
5. (a) Quan, L. G.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 3545.
6. (b) Gevorgyan, V.; Quan, L. G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4089.
7. Larock, R. C.; Tian, Q.; Pletnev, A. A. J. Am. Chem. Soc. 1999, 121, 3238.
8. 4NX is known. See: (b) Mori, M.; Kaneta, N.; Shibasaki, M. J. Organomet. Chem. 1994, 464, 35.
9. 4NX is known. See: (b) Mori, M.; Kaneta, N.; Shibasaki, M. J. Organomet. Chem. 1994, 464, 35.
10. 3 was also effective.
11. MeOH and EtOH were not examined since their boiling points were lower than the reaction temperatures.
12. Reduction of aryl halides to the corresponding dehalogenated arenes in the presence of palladium catalyst and base, see: (a) Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1978. (b) Tamaru, Y.; Yamamoto, Y.; Yamada, Y.; Yoshida, Z. Tetrahedron Lett. 1979, 16, 1401.
13. Reduction of aryl halides to the corresponding dehalogenated arenes in the presence of palladium catalyst and base, see: (a) Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1978. (b) Tamaru, Y.; Yamamoto, Y.; Yamada, Y.; Yoshida, Z. Tetrahedron Lett. 1979, 16, 1401.
14. Barnett, W. E.; Needham, L. L.; Powell, R. W. Tetrahedron, 1972, 28, 419.
15. 2)