Carbon-halogen bond activation by Nickel catalyst: Synthesis of alkenes, from 1,2-dihalides

Tetrahedron

Volumn 54, Issue 7, 1998, Pages 1021-1028

  Malanga, Corrado ^a   Mannucci, Serena ^a   Lardicci, Luciano ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; HALIDE; NICKEL COMPLEX; TIN DERIVATIVE;

ARTICLE; CATALYST; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032510179     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10203-4     Document Type: Article

References (23)

1. 1. McOmie, J. F. W. Protective Groups in Organic Chemistry; Plenum: New York, 1973.
2. 2. (a) Iyoda, M.; Sakaitani, M.; Kojima, A.; Oda, M. Tetrahedron Lett. 1985, 3719.
3. (b) Sarma, J. C.; Borbaruah, M.; Sharma, R. P. Tetrahedron Lett. 1985, 4657.
4. (c) Davies, S. G. ; Thomas, S. E. Synthesis 1984, 102.
5. 3. (a) Sugita, T.; Nakagawa, J.; Nishimoto, K. Bull. Chem. Soc. Jpn. 1979, 53, 871.
6. (b) Takeshi, O.; Teruaki, M. Chem. Lett. 1984, 12, 2069.
7. (c) Denichi, M.; Kazuo, I.; Toshikazu, S.; Ysauji, Y. Chem. Pharm. Bull. 1984, 32, 1840.
8. (d) Hitomi, S.; Masaiko, I. Chem. Lett. 1985, 2, 225.
9. (e) Ramendra, M.; James, H.; H. Synth. Commun. 1981, 11, 901.
10. (f) Schmidt, K. G. E. J. Organomet. Chem. 1980, 204, 393.
11. (g) Li, C. J.; Harpp, D. N. Tetrahedron Lett. 1990, 6291.
12. (h) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. Tetrahedron Lett. 1992, 5709.
13. (i) Baciocchi, E. in "1,2-dehalogenations and related reactions", Patai, S. and Rappoport, Z. The Chemistry of functional groups, sup.D, pg.161, Ed. Wiley, New York, 1983.
14. (l) Olah, G. A.; Surya Prakash, G. .K. Syntesis 1976, 607.
15. (m) Mathai, I. M.; Schug, K.; Miller, S. I. J. Org. Chem. 1970, 35, 1733.
16. (n) Gordon, J. E.; Chang, V. S. K. J. Org. Chem. 1973, 38, 3062.
17. (o) Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143.
18. 3. Malanga, C. ; Aronica, L. A. ; Lardicci, L. Tetrahedron Lett. 1995, 9189.
19. 4. The low yield obtained is probably due to the formation of the enolate of the ketone 2. Analogously, in the same reaction conditions adopted to convert 2 into 1, the phenyl chloromethyl ketone is converted to the corrsponding phenyl methyl ketone with a 50% overall yield.
20. 5. (a) Neuman, W. P. Synthesis 1987, 665.
21. (b) Dowd, P. ; Zhang, W. Chem. Rev. 1993, 2091.
22. (c) Enholm, E. J. ; Whithley, P. E. ; Xie, Y. J. Org. Chem. 1996, 61, 5384.
23. 6. Malanga, C. ; Urso, A. ; Lardicci, L. Tetrahedron Lett. 1995, 1133.