Organoaluminum-catalyzed new alkylation of tert-alkyl fluorides: Synthetic utility of Al-F interaction

Tetrahedron Letters

Volumn 38, Issue 32, 1997, Pages 5679-5682

  Ooi, Takashi ^a   Uraguchi, Daisuke ^a   Kagoshima, Naoko ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY;

EID: 0030861026     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01237-9     Document Type: Article

References (20)

1. Review: Reetz, M. T. Angew. Chem. Int. Ed. Engl. 1982, 21, 96. Nucleophilic displacement of vinyl fluoride by alkyllithium has been reported: Huot, J.-F.; Muzard, M.; Portella, C. Synlett 1995, 247.
2. Review: Reetz, M. T. Angew. Chem. Int. Ed. Engl. 1982, 21, 96. Nucleophilic displacement of vinyl fluoride by alkyllithium has been reported: Huot, J.-F.; Muzard, M.; Portella, C. Synlett 1995, 247.
3. Weast, R. C. Handbook of Chemistry and Physics; 65th Edition, CRC Press: New York, 1984-1985.
4. For the synthetic utility of forming the strong Al-F bonds, see: (a) Posner, G. H.; Ellis, J. W.; Ponton, J. J. Fluorine Chem. 1981, 19, 191.
5. (b) Posner, G. H.; Haines, S. R. Tetrahedron Lett. 1985, 26, 1823.
6. (c) Ooi, T.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. in press.
7. For example; (a) Middleton, W. J. J. Org. Chem. 1975, 40, 574.
8. (b) Mange, K. C.; Middleton, W. J. J. Fluorine Chem. 1989, 43, 405.
9. (c) Differding, E.; Duthaler, R. O.; Krieger, A.; Ruegg, G. M.; Schmit, C. Synlett 1991, 395.
10. (d) Pilcher, A. S.; Ammon, H. L.; DeShong, P. J. Am. Chem. Soc. 1995, 117, 5166.
11. see also: (e) Welch, J. T. Selective Fluorination in Organic and Bioorganic Chemistry; American Chemical Society, 1991.
12. tert-Alkyl fluoride 1 can be readily prepared from benzylacetone by the following sequences: (a) MeLi, ether, 0 °C;
13. 2, -78-20 °C (see ref. 4a).
14. 3-n (ACF). For the defluorination of perfluoroalkyl compounds mediated by aluminum halides, see: Krespan, C. G.; Petrov, V. A. Chem. Rev. 1996, 96, 3269.
15. Negishi, E.; Baba, S. J. Am. Chem. Soc. 1975, 97, 7385.
16. 13C NMR analysis. See: Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy; VCH: Weinheim, 1987.
17. 13C NMR spectrum. Generally, the equatorial-methyl signal of substituted cyclohexane derivatives appears downfield relative to the corresponding axial-methyl signal. See ref. 8.
18. (a) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wily & Sons: New York, 1991.
19. (b) Banks, R. E.; Smart, B. E.; Tatlow, J. C. Organofluorine Chemistry: Principles and Commercial Applications; Plenum Press: New York, 1994.
20. (c) Resnati, G. Tetrahedron 1993, 49, 9385.