Tetrakis(dimethylamino)ethylene (TDAE) as a potent organic electron source: Alkenylation of aldehydes using an Ni/Cr/TDAE redox system

Tetrahedron Letters

Volumn 41, Issue 1, 2000, Pages 81-84

  Kuroboshi, Manabu ^a   Tanaka, Muneaki ^a   Kishimoto, Suguru ^a   Goto, Kentaro ^a   Mochizuki, Misato ^a   Tanaka, Hideo ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Aldehydes; Alkenylation; Enamines; Reduction

Indexed keywords

ANISALDEHYDE; ENAMINE; ETHYLENE DERIVATIVE; STYRENE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; CROSS LINKING; ELECTROCHEMISTRY; OXIDATION REDUCTION REACTION;

EID: 0033992259     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02006-7     Document Type: Article

References (28)

1. (a) McMurry, J. E.; Lectka, T.; Rico, J. G. J. Org. Chem. 1989, 54, 3748.
2. (b) Betschart, C.; Seebach, D. Helv. Chim. Acta 1987, 70, 2215.
3. (c) Cahiez, G.; Chavant, P. Y. Tetrahedron Lett. 1989, 30, 7373. Hiyama, T.; Sawahata, M.; Obayashi, M. Chem. Lett. 1983, 1237.
4. (c) Cahiez, G.; Chavant, P. Y. Tetrahedron Lett. 1989, 30, 7373. Hiyama, T.; Sawahata, M.; Obayashi, M. Chem. Lett. 1983, 1237.
5. (d) Chan, M.-C.; Cheng, K.-M.; Ho, K. M.; Ng, C. T.; Yam, T. M.; Wang, B. S. L.; Luh, T.-Y. J. Org. Chem. 1988, 53, 4466.
6. Burkholder, C.; Dolbier Jr., W. R.; Médebielle, M. J. Org. Chem. 1998, 63, 5385.
7. (a) Chambers, R. D.; Nishimura, S.; Sandford, G. J. Fluorine Chem. 1998, 91, 63.
8. (b) Chambers, R. D.; Gray, W. K.; Korn, S. R. Tetrahedron 1995, 51, 13167.
9. (c) Chambers, R. D.; Vaughan, J. F. S.; Mullins, S. J.; Nakamura, T.; Roche, A. J. J. Fluorine Chem. 1995, 72, 231.
10. (d) Briscoe, M. W.; Chambers, R. D.; Mullins, S. J.; Nakamura, T.; Vaughan, J. F. S.; Drakesmith, F. G. J. Chem. Soc., Perkin Trans. 1 1994, 3115.
11. (e) Buerger, H.; Moritz, P. Organometallics 1993, 12, 4930.
12. (f) Burkholder, C.; Dolbier Jr., W. R.; Medebielle, M. Tetrahedron Lett. 1997, 38, 821.
13. (g) Pawelke, G. J. Fluorine Chem. 1991, 52, 229.
14. (h) Pawelke, G. J. Fluorine Chem. 1989, 42 429.
15. (a) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281.
16. For a recent review, see: (b) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1.
17. (a) Nicholas, A. S. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; 18 Schreber S. L. Pergamon Press: Oxford, 1991; Vol. 1, Chapter 1.6
18. (b) Cintas, P. Synthesis 1992, 248.
19. (c) Hoppe, D. In Methods of Organic Chemistry; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21, p. 1584.
20. (d) Jin, H.; Uenishi, J.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644.
21. (e) Dyer, U. C.; Kishi, Y. J. Org. Chem. 1988, 53, 3383.
22. (a) Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349.
23. (b) Kuroboshi, M.; Tanaka, M.; Kishimoto, S.; Goto, K.; Tanaka, H.; Torii, S. Tetrahedron Lett. in press.
24. Grigg, R., Putnikovic, B., Urch, C. J. Tetrahedron Lett. 1997, 38, 6307.
25. (d) Kuroboshi, M.; Tanaka, M.; Kishimoto, A.; Tanaka, H.; Torii, S. Synlett, 1999, 69.
26. 3 can promote the alkenylation reaction using Al as an electron source.
27. 2 conditions, 1-(4-chlorophenyl)-2-propen-1-ol was obtained in 25% (Ref. 6b).
28. 2 (Ref. 6b) conditions, respectively.