Collect. Czech. Chem. Commun. 2002, 67, 1467-1478
https://doi.org/10.1135/cccc20021467

Synthesis of 4-Fluorophenols from 4-tert-Butylphenols and Fluoride Sources Under Oxidative Conditions

Antoine Bienvenu, Audrey Barthelemy, Sarah Boichut, Bernard Marquet, Thierry Billard and Bernard R. Langlois*

Laboratoire SERCOF, UMR CNRS 5622, Université Claude Bernard-Lyon I, Bâtiment E. Chevreul, 43 Boulevard du 11 Novembre 1918, 69622 Villeurbanne cedex, France

References

1. Becker A.: Inventory of Industrial Fluoro-Biochemicals. Eyrolles, Paris 1996.
2. Clark J. H., Wails D., Bastock T. W.: Aromatic Fluorination. CRC, Boca Raton 1996.
3a. Banks R. E., Smart B. E., Tatlow J. C.: Organofluorine Chemistry: Principles and Commercial Applications. Plenum Press, New York 1994.
3b. Hudlický M., Pavlath A.: Chemistry of Organic Fluorine Compounds II. A Critical Review. American Chemical Society, Washington D. C. 1995.
4. Langlois B. R. in: Houben Weyl Methods of Organic Chemistry (B. Baasner, H. Hagemann and J. C. Tatlow, Eds), 4th ed., Vol. E10a, p. 686. Georg Thieme, Stuttgart 1999.
5a. Yoneda N.: Tetrahedron 1991, 47, 5329. <https://doi.org/10.1016/S0040-4020(01)80970-4>
5b. Fukuhara T., Yoneda N., Takamura K., Suzuki A.: J. Fluorine Chem. 1991, 51, 299. <https://doi.org/10.1016/S0022-1139(00)80301-2>
6a. Karam O., Jacquesy J. C., Jouannetaud M. P.: Tetrahedron Lett. 1994, 35, 2541. <https://doi.org/10.1016/S0040-4039(00)77165-6>
6b. Martin A., Jouannetaud M. P., Jacquesy J. C., Cousson A.: Tetrahedron Lett. 1996, 37, 7735. <https://doi.org/10.1016/0040-4039(96)01762-5>
6c. Karam O., Martin A., Jouannetaud M. P., Jacquesy J. C.: Tetrahedron Lett. 1999, 40, 4183. <https://doi.org/10.1016/S0040-4039(99)00718-2>
7. Stavber S., Jereb M., Zupan M.: Synlett 1999, 9, 1375. <https://doi.org/10.1055/s-1999-2840>
8. Barton D. H. R., Hesse R. H., Pechet M. M., Toh H. T.: J. Chem. Soc., Perkin Trans. 1 1974, 732. <https://doi.org/10.1039/p19740000732>
9. Mills J. S., Barrera J., Olivares E., Garcia H.: J. Am. Chem. Soc. 1960, 82, 5882. <https://doi.org/10.1021/ja01507a027>
10a. Pennington W. T., Resnati G., DesMarteau D. D.: J. Org. Chem. 1992, 57, 1536. <https://doi.org/10.1021/jo00031a038>
10b. Singh S., DesMarteau D. D., Zuberi S. S., Witz M., Huang H. N.: J. Am. Chem. Soc. 1987, 109, 7194. <https://doi.org/10.1021/ja00257a051>
11. Misaki S.: J. Fluorine Chem. 1981, 17, 159. <https://doi.org/10.1016/S0022-1139(00)85261-6>
12. Meurs J. H. H., Sopher D. W., Eilenberg W.: Angew. Chem., Int. Ed. Engl. 1989, 28, 927. <https://doi.org/10.1002/anie.198909271>
13. Eberson L., Hartshorn M. P., Persson O., Radner F.: Chem. Commun. 1996, 2105. <https://doi.org/10.1039/cc9960002105>
14. Kita Y., Tohma H., Inagaki M., Hatanaka K., Yakura T.: Tetrahedron Lett. 1991, 32, 4321. <https://doi.org/10.1016/S0040-4039(00)92160-9>
15. Kürti L., Herczegh P., Visy J., Simonyi M., Antus S., Pelter A.: J. Chem. Soc., Perkin Trans. 1 1999, 379. <https://doi.org/10.1039/a809206k>
16. Pelter A., Ward R. S.: Tetrahedron 2001, 57, 273. <https://doi.org/10.1016/S0040-4020(00)00935-2>