Ytterbium triflate-promoted tandem one-pot oxidation-cannizzaro reaction of aryl methyl ketones

Organic Letters

Volumn 7, Issue 7, 2005, Pages 1331-1333

  Curini, Massimo ^a   Epifano, Francesco ^a   Genovese, Salvatore ^a   Marcotullio, M Carla ^a   Rosati, Ornelio ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYACID; ACETONE; AROMATIC COMPOUND; ARYLACETIC ACID DERIVATIVE; ESTER; GLYOXAL DERIVATIVE; KETONE; SOLVENT; TRIFLUOROMETHANESULFONIC ACID; YTTERBIUM;

AQUEOUS SOLUTION; ARTICLE; CANNIZZARO REACTION; CATALYST; OXIDATION; PURIFICATION; SYNTHESIS;

EID: 17444410386     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050125e     Document Type: Article

References (22)

1. For a review, see: Geissman, T. A. Org. React. 1944, 2, 94-113.
2. Miersch, O.; Kramell, R.; Parthier, B.; Wastemack, C. Phytochemistry 1999, 50, 353-361.
3. Hoover, J. R. E.; Dunn, G. L.; Jakas, D. R.; Lam, L. L., Taggart, J. J.; Guarini, J. R.; Phillips, L. J. Med. Chem. 1974, 17, 34-41.
4. Nishihata, T.; Takahagi, H.; Yamamoto, M.; Tomida, M.; Rytting, J. H.; Higuchi, T. J. Pharm. Sci. 1984, 73, 109-113.
5. Yoshioka, M.; Yoshida, A.; Ichihashi, Y.; Saito, H. Chem Pharm. Bull. 1985, 33, 2145-2148.
6. El Nimr, A. E.; Salama, H. A.; Khalil, R. M.; Kassem, M. A. Pharmazie 1983, 38, 728-730.
7. Russell, A. E.; Miller, S. P.; Morken, J. P. J. Org. Chem. 2000, 65, 8381-8383.
8. (a) Maruyama, K.; Murakami, Y.; Yoda, K.; Mashino, T.; Nishinaga, A. J. Chem. Soc., Chem. Commun. 1992, 1617-1618.
9. (b) Jin, S. J.; Arora, P. K. Sayre, L. M. J. Org. Chem. 1990, 55, 3011-3018.
10. (c) Okuyama, T.; Kimura, K.; Fueno, T. Bull. Chem. Soc. Jpn. 1982, 55, 2285-2286.
11. Perchlorate salts pose an explosion hazard. See: Prudent Practices for Handling Hazardous Chemicals in Laboratories; National Academy Press: Washington, DC, 1981; p 65.
12. Chung, Y. M.; Gong, J. H.; Kim, J. N. Bull. Kor. Chem. Soc. 2002, 23, 1363-1364 and references therein.
13. (a) Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Tetrahedron Lett. 2001, 42, 3193-3195.
14. (b) Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Eur. J. Org. Chem. 2002, 1562-1565.
15. (c) Curini, M.; Epifano, F.; Maltese, F.; Rosati, O. Tetrahedron Lett. 2002, 43, 4895-4897.
16. (d) Curini, M.; Epifano, F.; Maltese, F.; Rosati, O. Synlett 2003, 552-554.
17. (e) Curini, M.; Epifano, F.; Maltese, F.; Marcotullio, M. C. Eur. J. Org. Chem. 2003, 1631-1634.
18. (f) Curini, M.; Epifano, F.; Montanari, F.; Rosati, O.; Taccone, S. Synlett 2004, 1832-1834.
19. Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. L. Chem. Rev. 2002, 6, 2227-2302.
20. Fuson, R. C.; Emerson, W. S.; Gray, H. W. J. Am. Chem. Soc. 1939, 61, 480-482.
21. Pitzer, K. S. Acc. Chem. Res. 1974, 12, 271-276.
22. Fieser, M. Reagents for Organic Synthesis; Wiley-Interscience: New York; Vol. 14, p 188.