Dichloromethane activation. Direct methylenation of ketones and aldehydes with CH2Cl2 promoted by Mg/TiCl4/THF

Organic Letters

Volumn 6, Issue 26, 2004, Pages 4961-4963

  Yan, Tu Hsin ^a   Tsai, Chia Chung ^a   Chien, Ching Ting ^a   Cho, Chia Ching ^a   Huang, Pei Chen ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; CHLORINE DERIVATIVE; DICHLOROMETHANE; KETONE DERIVATIVE; MAGNESIUM CHLORIDE; TITANIUM TETRACHLORIDE;

ARTICLE; METHYLATION; QUANTUM YIELD; REACTION ANALYSIS; TRANSPORT KINETICS;

EID: 12344292465     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0478887     Document Type: Article

References (22)

1. (a) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611.
2. (b) Pine, S. H.; Zahier, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270.
3. (a) Takai, K.; Hotta, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1978, 19, 2417.
4. (b) Lombardo, L. Org. Synth. 1987, 65, 81.
5. (c) Hibino, J.; Okazoe, T.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.
6. (d) Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668
7. Petasis, N. A.; Bzoweej, E. I. J. Am. Chem. Soc. 1990, 112, 6392.
8. (a) Bertini, F.; Grasselli, P.; Zubiani, G.; Cainelli, G. Tetrahedron 1970, 26, 1281.
9. (b) van de Heisteeg, B. J. J.; Schat, G.; Akkerman, O. S.; Bickelhaupt, F. J. Organomet. Chem. 1985, 308, 1.
10. Barluenga, J.; Fernandez-Simon, J. L.; Concellon, J. M.; Yus, M. J. Chem. Soc., Chem. Commun. 1986, 1665.
11. Aleandri, L. E.; Bogdanovic, B.; Gaidies, A.; Jones S. Liao, D. J.; Michalowicz, A.; Roziere, J.; Schott, A. J. Organomet. Chem. 1993, 459, 87.
12. 2 in the presence of THF.
13. Corey, E. J.; Danheiser, R. L.; Chandrasekaran, S. J. Org. Chem. 1976, 41, 260.
14. (a) Dams, R.; Malinowski, M.; Westdorp, I.; Geise, H. J. J. Org. Chem. 1982, 47, 248.
15. (b) Lenoir, D. Synthesis 1989, 885.
16. McMurry, J. E.; Fleming, M. P. J. Org. Chem. 1976, 41, 896.
17. Johnson, C. R.; Tait, B. D. J. Org. Chem. 1987, 52, 281.
18. Clawson, L.; Buchwald, S. L.; Grubbs, R. H. Tetrahedron Lett. 1984, 25, 5733.
19. Corey, E. J.; Kang, J.; Kyler, K. Tetrahedron Lett. 1985, 26, 555.
20. Akgun, E.; Mahmood, K.; Mathis, C. A. J. Chem. Soc., Chem. Commun. 1994, 761.
21. n]-catalyzed cleavage of ethers, see: (a) Bartmann, E. J. Organomet, Chem. 1985, 284, 149. (b) Kadam, S. M.; Nayak, S. K.; Banerji, A. Tetrahedron Lett. 1992, 33, 5129.
22. n]-catalyzed cleavage of ethers, see: (a) Bartmann, E. J. Organomet, Chem. 1985, 284, 149. (b) Kadam, S. M.; Nayak, S. K.; Banerji, A. Tetrahedron Lett. 1992, 33, 5129.