Facile preparation of fluorine-containing alkenes, amides and alcohols via the electrophilic fluorination of alkenyl boronic acids and trifluoroborates

Synlett

Volumn , Issue 5, 1997, Pages 606-608

  Petasis, Nicos A ^a   Yudin, Andrei K ^a   Zavialov, Ilia A ^a   Prakash, G K Surya ^a   Olah, George A ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000213491     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3228     Document Type: Article

References (25)

1. (a) Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications; Elsevier: Amsterdam, 1993.
2. (b) Kukhar, V. P.; Soloshonok, V. A., Eds. Fluorine-Containing Amino Acids: Synthesis and Properties; John Wiley & Sons: Chichester, 1995.
3. (c) Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds. Biomedical Frontiers of Fluorine Chemistry; American Chemical Society: Washington DC, 1996.
4. (a) Olah, G. A.; Chambers, R. D.; Prakash, G. K. S. Eds. Synthetic Fluorine Chemistry; John Wiley & Sons: New York, 1992.
5. (b) Banks, R. E.; Smart, B. E.; Tatlow, J. C. Organofluorine Chemistry: Principles and Commercial Applications; Plenum Press: New York, 1994.
6. (c) Percy, J. M. Contemp. Org. Synth. 1996, 251.
7. (a) Prakash, G. K. S.; Krishnamurti, R.; Olah, G. A. J. Am. Chem. Soc. 1989, 111, 393.
8. (b) Prakash, G. K. S.; Yudin, A. K.; Deffieux, D.; Olah, G. A. Synlett 1996, 151.
9. Yudin, A. K.; Prakash, G. K. S.; Deffieux, D.; Bradley, M.; Bau, R.; Olah, G. A. J. Am. Chem. Soc. 1997, 119, 1572.
10. (a) For an alternative synthesis of trifluoromethylated amides see: Tongco, E. C.; Prakash, G. K. S.; Olah, G. A. Synlett, submitted for publication.
11. (b) For other synthetic approaches and medicinal applications of fluorinated amino alcohols see: Begué, J.-P.; Bonnet-Delpon, D. in ref. 1 (c), p.59.
12. For a review see: Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619.
13. For a review see: Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737.
14. Petasis, N. A.; Zavialov, I. A. Tetrahedron Lett. 1996, 37, 567.
15. Matthews, D. P.; Miller, S. C; Jarvi, E. T.; Sabol, J. S.; McCarthy, J. R. Tetrahedron Lett. 1993, 34, 3057.
16. Lal, G. S. J. Org. Chem. 1993, 58, 2791.
17. Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1975, 97, 5249.
18. 3CN) δ-140 (br).
19. Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3020.
20. 3) δ -122.6 (dd, J = 84 Hz, 45 Hz).
21. 3) δ -128.6 (ddd, J = 280 Hz, 56 Hz, 10.5 Hz, 1F), - 126.2 (ddd, J = 280 Hz, 56 Hz, 10.5 Hz, 1F). (Lit.: Hagiwara, T.; Fuchikami, T. Synlett, 1995, 717).
22. 2 200.0889, found 200.0887.
23. (a) Krimen, L. I.; Cota, D. J. Org. React 1969, 17, 213.
24. (b) Bishop, R. in Comprehensive Organic Synthesis, Trost, B. M.; Flemming, I., Eds.; Pergamon: Oxford, 1991, Vol. 6, 261.
25. For another type of Ritter reaction initiated by Selectfluor™ see: Banks, R. E.; Lawrence, N. J.; Besheesh, M. K.; Popplewell, A. L.; Pritchard, R. G. Chem. Commun. 1996, 1629.