Layered double hydroxides exchanged with tungstate as biomimetic catalysts for mild oxidative bromination

Nature

Volumn 400, Issue 6747, 1999, Pages 855-857

  Sels, Bert ^a   De Vos, Dirk ^a   Buntinx, Mieke ^a   Plerard, Frédéric ^b   Kirsch De Mesmaeker, A ^b   Jacobs, Pierre ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

^b UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE COMPOUNDS; CATALYST ACTIVITY; HALOGENATION; TUNGSTEN COMPOUNDS;

BIOMIMETIC CATALYSTS; BROMINATION; EPOXIDATION; HYDROXIDES; TUNGSTATES;

CATALYSTS;

BROMINE; HYDROGEN PEROXIDE; HYDROXIDE; PEROXIDASE; TUNGSTEN;

ACIDITY; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; COST; DRUG MANUFACTURE; EPOXIDATION; HALOGENATION; HEALTH HAZARD; OXIDATION; PH; PRIORITY JOURNAL; REACTION ANALYSIS; SAFETY; TEMPERATURE;

EID: 0033607004     PISSN: 00280836     EISSN: None     Source Type: Journal    
DOI: 10.1038/23674     Document Type: Article

References (31)

1. Ullmann's Encyclopedia of Industrial Chemistry 6th edn (Electronic release, Wiley-VCH, Weinheim, 1998).
2. Gribble, G. W. Naturally occurring organohalogen compounds. Acc. Chem. Res. 31, 141-152 (1998).
3. Butler, A. & Walker, J. V. Marine haloperoxidases. Chem. Rev. 93, 1937-1944 (1993).
4. Franssen, M. C. R. & van der Plas, H. C. Haloperoxidases: their properties and their use in organic synthesis. Adv. Appl. Microbiol. 37, 41-99 (1992).
5. Butler, A. in Bioinorganic Catalysis (ed. Reedijk, J.) Ch. 13 (Dekker, New York, 1993).
6. Conte, V., Di Furia, F. & Moro, S. Mimicking the vanadium bromoperoxidase reactions: mild and selective bromination of arenes and alkenes in a two-phase system. Tetrahedr. Lett. 35, 7429-7432 (1994).
7. Reynolds, M. S., Morandi, S. J., Raebiger, J. W., Melican, S. P. & Smith, S. P. E. Kinetics of bromide oxidation by (oxalato)oxodiperoxomolybdate(VI). Inorg. Chem. 33, 4977-4984 (1994).
8. Espenson, J. H., Pestovsky, O., Huston, P. & Staudt, S. Organometallic catalysis in aqueous solution: oxygen transfer to bromide. J. Am. Chem. Soc. 116, 2869-2877 (1994).
9. Clague, M. J. & Butler, A. On the mechanism of cis-dioxovanadium(V)-catalyzed oxidation of bromide by hydrogen peroxide: evidence for a reactive, binuclear vanadium(V) peroxo complex. J. Am. Chem. Soc. 117, 3475-3484 (1995).
10. Meister, G. E. & Butler, A. Molybdenum(VI)- and tungsten(VI)-mediated biomimetic chemistry of vanadium bromoperoxidase. Inorg. Chem. 33, 3269-3275 (1994).
11. Hamstra, B. J., Colpas, G. J. & Pecoraro, V. L. Reactivity of dioxovanadium(V) complexes with hydrogen peroxide: implications for vanadium haloperoxidase. Inorg. Chem. 37, 949-955 (1998).
12. Walker, J. V. et al. Peroxidative halogenation catalyzed by transition-metal-ion-grafted mesoporous silicate materials. J. Am. Chem. Soc. 119, 6921-6922 (1997).
13. Trifirò, F. & Vaccari, A. in Comprehensive Supramolecular Chemistry Vol. 7, 251 (Pergamon, Elsevier Science, Oxford, 1996).
14. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds (Wiley-Interscience, New York, 1986).
15. Soedjak, H. S. & Butler, A. Mechanism of dioxygen formation catalyzed by vanadium bromoperoxidase from Macrocystis pyrifera and Fucus distichus: steady state kinetic analysis and comparison to the mechanism of V-BrPO from Ascophyllum nodosum. Biochem. Biophys. Acta 1079, 1-7 (1991).
16. Held, A. M., Halko, D. J. & Hurst, J. K. Mechanisms of chlorine oxidation of hydrogen peroxide. J. Am. Chem. Soc. 100, 5732-5740 (1978).
17. Everett, R. R., Kanofsky, J. R. & Butler, A. Mechanistic investigations of the novel non-heme Vanadium bromoperoxidases. J. Biol. Chem. 265, 4908-4914 (1990).
18. Primer, A. A. Singlet Oxygen (CRC, Boca Raton, Florida, 1985).
19. Schubert, W. M. & Keeffe, J. R. The acid-catalyzed hydration of styrenes. J. Am Chem. Soc. 94, 559-566 (1972).
20. Yates, K., McDonald, R. S. & Shapiro, S. A. Kinetics and mechanisms of electrophilic addition. I. A comparison of second- and third-order brominations. J. Org. Chem. 38, 2460-2463 (1973).
21. Messerschmidt, A. & Wever, R. X-ray structure of a vanadium-containing enzyme. Chloroperoxidase from the fungus Curvularia inaequalis. Proc. Natl. Acad. Sci. USA 93, 392-396 (1996).
22. Kresge, C. T., Leonowicz, M. E., Roth, W. J., Vartuli, J. C. & Beck, J. S. Ordered mesoporous molecular sieves synthesized by a liquid-crystal template mechanism. Nature 359, 710-712 (1992).
23. Maschmeyer, T., Rey, T., Sankar, F. & Thomas, J. M. Heterogeneous catalysts obtained by grafting metallocene complexes onto mesoporous silica. Nature 378, 159-162 (1996).
24. Huybrechts, D. R. C., De Bruycker, L. & Jacobs, P. A. Oxyfunctionalization of alkanes with hydrogen peroxide on titanium silicalite. Nature 345, 240-242 (1990).
25. Knops-Gerrits, P.-P., De Vos, D., Thibault-Starzyk, F. & Jacobs, P. A. Zeolite-encapsulated Mn(u) complexes as catalysts for selective alkene oxidation. Nature 369, 543-546 (1994).
26. Kadima, T. A. & Pickard, M. A. Immobilization of chloroperoxidase on aminopropyl-glass. Appl. Environ. Microbiol. 56, 3473-3477 (1990).
27. Roouhi, M. New reaction uncouples epoxidation from acidity. Chem. Eng. News 7 July, 6-7 (1997).
28. Itoh, N., Cheng, L, Izumi, Y. & Yamada, H. Immobilized bromoperoxidase of Corallina pilulifera as a multifunctional halogenating biocatalyst. J. Biotechnol. 5, 29-38 (1987)
29. Aoun, S. & Baboulène, M. Regioselective bromohydroxylation of alkenes catalyzed by chloroperoxidase: Advantages of the immobilization on talc. J. Mol. Catal. B 4, 101-109 (1998).
30. Sheldon, R. A. & Kochi, J. K. Metal-Catalyzed Oxidation of Organic Compounds (Academic, New York, 1981).
31. Sels, B. F., De Vos, D. E. & Jacobs, P. A. Selective epoxidations involving anionic peroxotungsten compounds generated in situ on layered double hydroxides with various polarities. Tetrahedr. Lett. 37, 8557-8560 (1996).