Controlling chemoselectivity in reactions of unprotected naphthalene-1-carboxylic acid with strong bases

Chemistry Letters

Volumn 34, Issue 3, 2005, Pages 446-447

  Tilly, David ^a   Castanet, Anne Sophie ^a   Mortier, Jacques ^a  

^a UNIVERSITÉ DU MAINE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; CARBOXYLIC ACID DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION;

EID: 19444387314     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.446     Document Type: Article

References (26)

1. J. A. Dixon, D. H. Fishman, and R. S. Dudinyak, Tetrahedron Lett., 5, 613 (1964).
2. M. Shindo, K. Koga, and K. Tomioka, J. Org. Chem., 63, 9351 (1998).
3. L. F. S. V. Kolotuchin and A. I. Meyers, J. Org. Chem., 65, 3018 (2000), and references cited therein.
4. M. Shindo, K. Koga, Y. Asano, and K. Tomioka, Tetrahedron, 55, 4955 (1999).
5. B. Plunian, M. Vaultier, and J. Mortier, J. Chem. Soc., Chem. Commun., 1998, 81.
6. B. Plunian, J. Mortier, M. Vaultier, and L. Toupet, J. Org. Chem., 61, 5206 (1996).
7. J. Clayden, C. S. Frampton, C. McCarthy, and N. Westlund, Tetrahedron, 55, 14161 (1999), and references cited therein.
8. Review: N. S. Narasimhan and R. S. Mali, Synthesis, 1983, 957.
9. J. Mortier, J. Moyroud, B. Bennetau, and P. A. Cain, J. Org. Chem., 59, 4042 (1994);
10. Review: J. Mortier and M. Vaultier, in "Recent Research Developments in Organic Chemistry," Transworld Research Network, Trivandrum (1998), Vol. 2, p 269.
11. C. G. Hartung and V. Snieckus, "Modern Arene Chemistry," ed. by D. Astruc, Wiley-VCH, New York (2002), p 330.
12. F. Gohier, A.-S. Castanet, and J. Mortier, Org. Lett., 5, 1919 (2003).
13. F. Gohier and J. Mortier, J. Org. Chem., 68, 2030 (2003).
14. F. Gohier, A.-S. Castanet, and J. Mortier, J. Org. Chem., 70, (2005), in press.
15. L. Lochmann, Eur. J. Inorg. Chem., 2000, 1115.
16. F. Mongin, R. Maggi, and M. Schlosser, Chimia, 50, 650 (1996).
17. M. Watanabe and V. Snieckus, J. Am. Chem. Soc., 102, 1457 (1980);
18. V. Snieckus, Chem. Rev., 90, 879 (1990).
19. S. O. De Silva, J. N. Reed, R. J. Billedeau, X. Wang, D. J. Norris, and V. Snieckus, Tetrahedron, 48, 4863 (1992).
20. T. D. Krizan and J. C. Martin, J. Am. Chem. Soc., 105, 6155 (1983).
21. Dimethyl sulfate and n-butyllithium are also mutually compatible in THF at -78°C: G. C. Nwokogu and H. Hart, Tetrahedron Lett., 24, 5725 (1983).
22. R. Taylor, Tetrahedron Lett., 16, 435 (1975).
23. S. Caron and J. M. Hawkins, J. Org. Chem., 63, 2054 (1998).
24. 1H NMR and FIMS. The error is taken to be ±5%.
25. W. Bauer and L. Lochmann, J. Am. Chem. Soc., 114, 7482 (1992).
26. General procedure: To a stirred solution of naphthalene-1-carboxylic acid (1) (300 mg, 1.74 mmol) in anhydrous THF (15 mL) at -78°C, was added the precooled (-78°C) THF solution (10mL) of the LiCKOR base (6.96 mmol, 4equiv.). The reaction mixture was allowed to warm up to -50°C and stirred at this temperature for 3 h. The electrophile (6-10 equiv.) in THF (8 mL) was then added. The reaction mixture was allowed to warm to room temperature over a period of 2 h. Acidification and standard workup led to a residue which was purified by chromatography on silicagel using cyclohexane/ethyl acetate (90:10) followed by recrystallization (heptane/ethyl acetate).