In/InCl3-mediated cross-coupling reactions of methyl vinyl ketone with benzaldehyde in aqueous media

Organic Letters

Volumn 2, Issue 23, 2000, Pages 3615-3617

  Kang, Soyeon ^a,b   Jang, Taeg Su ^a   Keum, Gyochang ^a   Kang, Soon Bang ^a   Han, So Yeop ^b   Kim, Youseung ^a  

^a Korea Institute of Science and Technology   (South Korea)

^b Ewha Womans University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001664363     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006495e     Document Type: Article

References (22)

1. Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons, Inc.: New York, 1997.
2. (a) Cintas, P. Synlett 1995, 1087.
3. (b) Hashmi, A. S. K. J. Prakt. Chem. 1998, 340, 84.
4. Lim, H. J.; Keum, G.; Kang, S. B.; Chung, B. Y.; Kim, Y. Tetrahedron Lett. 1998, 39, 4367.
5. Chae, H.; Cho, S.; Keum, G.; Kang, S. B.; Pae, A. N.; Kim, Y. Tetrahedron Lett. 2000, 41, 3899.
6. (a) Wang, L.; Sun, X.; Zhang, Y. Synth. Comm. 1998, 28, 3263.
7. (b) Bergman, E. D.; Ginsburg, D.; Rappo, R. Org. React. 1959, 10, 179.
8. (a) Valle, L. D.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019.
9. (b) Chang, S.; Yoon, J.; Brookhart, M. J. Am. Chem. Soc. 1994, 116, 1869.
10. (c) Yoshida, H.; Oomori, K.; Miyata, H.; Onzuka, K.; Fuse, K. JP 08081406, 1996; Chem. Abstr. 1996, 125, 57554.
11. 2O (1:2, 3 mL) was stirred at ambient temperature for 6 h. After the addition of 1 N HCl (1.5 mL), the reaction mixture was stirred for 30 min and extracted with ethyl acetate (15 mL x 3). The combined organic phase was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel with a mixture of hexane and ethyl acetate (10:1) to give 5-(4-fluorophenyl)-4-penten-2-one (70.6 mg, 79% yield).
12. In the absence of MVK, the pinacol product of cinnamaldehyde was isolated in 79% yield as a mixture of dl and meso isomers (84:16).
13. Two types of radical-anion (1,2- and 1,4-) of methyl vinyl ketone were possible. See: Pons, J.-M.; Zahra, J.-P.; Santelli, M. Tetrahedron Lett. 1981, 22, 3965.
14. The retardation was analyzed by GC yield of the product formed. In the absence of BHT, the β,γ-unsaturated ketone was formed in 35% and 81% yield after 1 h and 4 h, respectively. In the presence of 0.1 equiv of BHT, however, the corresponding yields were 28% and 53% and under 0.5 equiv of BHT, the results were 5% and 15% yields, respectively.
15. 2O) δ 7.4 (m, 5H), 4.9-4.2 (m, 1H), 2.5-2.0 (4s, 3H), 1.2-0.5 (m, 3H).
16. 2: Toratsu, C.; Fujii, T.; Suzuki, T.; Takai, K. Angew. Chem., Int. Ed. 2000, 39, 2725.
17. 2: Montgomery, D.; Reynolds, K.; Stevenson, P. J. Chem. Soc., Chem. Commun. 1993, 363.;
18. 4 (cat.): Sato, T.; Watanabe, M.; Watanabe, T.; Onoda, Y.;, Murayama, E. J. Org. Chem. 1988, 53, 1894.
19. (d) With Zn/HCl: Elphimoff-Felkin, I.; Sadra, P. Tetrahedron 1975, 31, 2781.
20. Examples of the ring-opening reactions of cyclopropanols: (a) Corey, E. J.; Ulrich, P. Tetrahedron Lett. 1975, 3685.
21. (b) Gibson, D. H.; DePuy, C. H. Chem. Rev. 1974, 74, 605. and see ref 12a.
22. 3) δ 7.38-7.19 (m, 5H), 6.46 (d, J = 16.0 Hz. 1H), 6.30 (dt, J = 15.9, 6.9 Hz, 2H), 3.32 (d, J = 6.9 Hz, 2H), 2.19 (s. 3H).