cis-Dihydroxylation and epoxidation of alkenes by [Mn2O(RCO 2)2(tmtacn)2]: Tailoring the selectivity of a highly H2O2-efficient catalyst

Journal of the American Chemical Society

Volumn 127, Issue 22, 2005, Pages 7990-7991

  De Boer, Johannes W ^a   Brinksma, Jelle ^a,b   Browne, Wesley R ^a   Meetsma, Auke ^a   Alsters, Paul L ^c   Hage, Ronald ^d   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b Kiadis BV   (Netherlands)

^c Catalysis and Development   (Netherlands)

^d UNILEVER RESEARCH VLAARDINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

1 OCTENE; 2,6 DICHLOROBENZOIC ACID; ALKENE; BENZOIC ACID DERIVATIVE; CARBOXYLIC ACID; CATALASE; CYCLOHEXENE; CYCLOOCTENE; HYDROGEN PEROXIDE; MANGANESE DERIVATIVE; SALICYLIC ACID; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CATALYST; COMPLEX FORMATION; DIHYDROXYLATION; EPOXIDATION; MASS SPECTROMETRY; ORGANIC CHEMISTRY; OXIDATION; SYNTHESIS; X RAY ANALYSIS;

EID: 20444417131     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050990u     Document Type: Article

References (29)

1. (a) Lane, B. S.; Burgess, K. Chem. Rev. 2003, 103, 2457-2473.
2. (b) Sheldon, R. A.; Kochi, J. K. Metal-Catalysed Oxidations of Organic Compounds; Academic Press: New York, 1981.
3. (c) Brinksma, J.; de Boer, J. W.; Hage, R.; Feringa, B. L. Modern Oxidation Methods; Bäckvall, J.-E., Ed.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 10, pp 295-326.
4. (d) Noyori, R.; Aoki, M.; Sato, K. Chem. Commun. 2003, 1977-1986.
5. (e) Katsuki T. Chem. Soc. Rev. 2004, 33, 437-444.
6. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
7. (a) Nelson, D. W.; Gypser, A.; Ho, P. T.; Kolb, H. C.; Kondo, T.; Kwong, H.-L.; McGrath, D. V.; Rubin, A. E.; Norrby, P.-O.; Gable, K. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 1840-1858.
8. (b) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
9. (c) Sato, K.; Aoki, M.; Ogawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310-8311.
10. (d) Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Eng. 1991, 30, 1638-1641.
11. Lane, B. S.; Vogt, M.; DeRose, V. J.; Burgess, K. J. Am. Chem. Soc. 2002, 124, 11946-11954.
12. (a) Fujita, M.; Costas, M.; Que, L., Jr. J. Am. Chem. Soc. 2003, 125, 9912-9913.
13. (b) Chen, K.; Costas, M.; Kim, J.; Tipton, A. K.; Que, L., Jr. J. Am. Chem. Soc. 2002, 124, 3026-3035.
14. (c) Ryu, J. Y.; Kim, J.; Costas, M.; Chen, K.; Nam, W.; Que, L., Jr. Chem. Commun. 2002, 1288-1289.
15. White, M. C.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 7194-7195.
16. De Vos, D. E.; De Wildeman, S.; Sels, B. F.; Grobet, P. J.; Jacobs, P. A. Angew. Chem., Int. Ed. 1999, 38, 980-983.
17. Brinksma, J.; Schmieder, L.; Van Vliet, G.; Boaron, R.; Hage, R.; De Vos, D. E.; Alsters, P. L.; Feringa, B. L. Tetrahedron Lett. 2002, 43, 2619-2622.
18. (a) Hage, R.; Iburg, J. E.; Kerschner, J.; Koek, J. H.; Lempers, E. L. M.; Martens, R. J.; Racherla, U. S.; Russell, S. W.; Swanhoff, T.; van Vliet, M. R. P.; Warnaar, J. B.; van der Wolf, L.; Krijnen, B. Nature 1994, 369, 637-639.
19. (b) De Vos, D. E.; Bein, T. Chem. Commun. 1996, 917-918.
20. (c) Zondervan, C.; Hage, R.; Feringa, B. L. Chem. Commun. 1997, 419-420.
21. (d) De Vos, D. E.; Sels, B. F.; Reynaers, M.; Subba Rao, Y. V.; Jacobs, P. A. Tetrahedron Lett. 1998, 39, 3221-3224.
22. (e) Berkessel, A.; Sklorz, C. A. Tetrahedron Lett. 1999, 40, 7965-7968.
23. (f) Woitiski, C. B.; Kozlov, Y. N.; Mandelli, D.; Nizova, G. V.; Schuchardt, U.; Shul'pin, G. B. J. Mol. Catal. A 2004, 222, 103-119.
24. Tmtacn; N,N′,N″-trimethyl-1,4,7-triazacyclononane.
25. Wieghardt, K.; Bossek, U.; Nuber, B.; Weiss, J.; Bonvoisin, J.; Corbella, M.; Vitols, S. E.; Girerd J. J. J. Am. Chem. Soc. 1988, 110, 7398-7411.
26. See Supporting Information.
27. Control experiments confirmed that peracid formation, if it occurs, does not induce any cis-dihydroxylation.
28. Hage, R.; Krijnen, B.; Warnaar, J. B.; Hard, F.; Stufkens, D. J.; Snoeck T. L. Inorg. Chem. 1995, 34, 4973-4978.
29. Competing oxidation processes make a significant contribution to the reduced cis-diol/epoxide yield; see Table S3.