Iron-substituted polyoxotungstates as inorganic synzymes: Evidence for a biomimetic pathway in the catalytic oxygenation of catechols

Chemistry - A European Journal

Volumn 15, Issue 32, 2009, Pages 7854-7858

  Sartorel, Andrea ^b   Carraro, Mauro ^b   Scorrano, Gianfranco ^b   Bassil, Bassem S ^a   Dickman, Michael H ^a   Keita, Bineta ^c   Nadjo, Louis ^c   Kortz, Ulrich ^a   Bonchio, Marcella ^b  

^a JACOBS UNIVERSITY BREMEN   (Germany)

^b UNIVERSITY OF PADOVA   (Italy)

^c CNRS   (France)

Author keywords

Catechol cleavage; Homogeneous catalysis; Iron; Polyoxometalates; Synzymes

Indexed keywords

BIO-INSPIRED; BIOMIMETIC PATHWAYS; CATALYTIC OXYGENATION; CATECHOL CLEAVAGE; CATECHOLATE; CHARGE TRANSFER BANDS; CHARGE TRANSFER TRANSITIONS; CLEAVAGE PRODUCTS; HOMOGENEOUS CATALYSIS; IRON CENTERS; LEWIS ACIDITY; NIR SPECTRUM; POLYOXOMETALATES; POLYOXOTUNGSTATES; POLYTUNGSTATES; SENSITIVE PROBE; STRUCTURE-REACTIVITY RELATIONSHIPS; SYNZYMES;

BIOMETRICS; BIOMIMETICS; CHARGE TRANSFER; ION EXCHANGE; OXYGENATION; REACTION KINETICS;

CATALYSIS;

CATECHOL DERIVATIVE; IRON; ORGANOMETALLIC COMPOUND; PROTOCATECHUATE 3,4 DIOXYGENASE; TUNGSTEN;

ARTICLE; CATALYSIS; CHEMISTRY; METABOLISM; OXIDATION REDUCTION REACTION;

CATALYSIS; CATECHOLS; IRON; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PROTOCATECHUATE-3,4-DIOXYGENASE; TUNGSTEN;

EID: 68349098381     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901392     Document Type: Article

References (51)

1. J. S. Valentine, C. S. Foote, A. Greenberg, J.F. Liebman in Active Oxygen in Biochemistry, St. Edmundsbury, London, 1995.
2. T. Punniyamurthy, S. Velusamy, J. Iqbal, Chem. Rev. 2005, 105, 2329-2364.
3. R. Breslow, Acc. Chem. Res. 1995, 28, 146-153.
4. B. J. Wallar, J. D. Lipscomb, Chem. Rev. 1996, 96, 2625-2658.
5. Special Issue "Polyoxometalates": Chem. Rev. 1998, 98, 1-387, edited by C. L. Hill.
6. M. T. Pope, A. Müller in Polyoxometalate Chemistry: From Topology via Self-assembly to Applications, Kluwer, Dordrecht, 2002.
7. C. L. Hill, C. M. Prosser-McCharta, Coord. Chem. Rev. 1995, 143, 407-455.
8. a) M. Costas, M. P. Mehn, M. P. Jensen, L. Que, Jr., Chem. Rev. 2004, 104, 939-986;
9. b) P. C. A. Bruijnincx, G. van Koten, R. J. M. Klein Gebbink, Chem. Soc. Rev. 2008, 37, 2716-2744.
10. T. J. McMurry, J. T. Groves in Metalloporphyrin Models for Cytochrome P-450 (Ed.: P. R. Ortiz de Montellano), Plenum Press, New York, 1986.
11. a) D. K. Lyon, W. K. Miller, T. Novet, P. J. Domaille, E. Evitt, D. C. Johnson, R. G. Finke, J. Am. Chem. Soc. 1991, 113, 7209-7221;
12. b) D. Mansuy, J. F. Bartoli, P. Battioni, D. K. Lyon, R. G. Finke, J. Am. Chem. Soc. 1991, 113, 7222-7226.
13. Y. Nishiyama, Y. Nakagawa, N. Mizuno, Angew. Chem. 2001, 113, 3751-3753;
14. Angew. Chem. Int. Ed. 2001, 40, 3639-3641.
15. S. Shaik, H. Hirao, D. Kumar, Acc. Chem. Res. 2007, 40, 532-542.
16. a) D. Kumar, E. Derat, A. M. Khenkin, R. Neumann, S. Shaik, J. Am. Chem. Soc. 2005, 127, 17712-17718;
17. b) E. Derat, D. Kumar, R. Neumann, S. Shaik, Inorg. Chem. 2006, 45, 8655-8663;
18. c) D. Barats, G. Leitus, R. Popovitz-Biro, L. J. W. Shimon, R. Neumann, Angew. Chem. 2008, 120, 10056-10060;
19. Angew. Chem. Int. Ed. 2008, 47, 9908-9912.
20. a) A. Sartorel, M. Carrara, G. Scorrano, R. De Zorzi, S. Geremia, N. D. McDaniel, S. Bernhard, M. Bonchio, J. Am. Chem. Soc. 2008, 130, 5006;
21. b) G. Süss-Fink, Angew. Chem. 2008, 120, 5972-5974;
22. Angew. Chem. Int. Ed. 2008, 47, 5888-5890.
23. C. X. Yin, R. G. Finke, Inorg. Chem. 2005, 44, 4175-4188.
24. a) B. Botar, Y. V. Geletii, P. Kögerler, D. G. Musaev, K. Morokuma, I.A. Weinstock, C.L. Hill, J. Am. Chem. Soc. 2006, 128, 1126811277;
25. b) M. Bonchio, M. Carrara, A. Farinazzo, A. Sartorel, G. Scorrano, U. Kortz, J. Mol. Catai. A 2007, 262, 36-40.
26. M. Bonchio, M. Carrara, A. Sartorel, G. Scorrano, U. Kortz, J. Mol. Catal. A 2006, 251, 93-99.
27. U. Kortz, M. G. Savelieff, B. S. Bassil, B. Keita, L. Nadjo, Inorg. Chem. 2002, 41, 783-789.
28. a) H. Weiner, Y. Hayashi, R. G. Finke, Inorg. Chim. Acta 1999, 291, 426-437;
29. b) H. Weiner, R. G. Finke, J. Am. Chem. Soc. 1999, 121, 9831-9842 and references therein;
30. c) C. X. Yin, R. G. Finke, J. Am. Chem. Soc. 2005, 127, 9003-9013.
31. a) Oxygenases and Model Systems (Ed.: T. Funabiki), Kluwer, Dordrecht, 1997;
32. b) L. Que, Jr., R. Y. N. Ho, Chem. Rev. 1996, 96, 26072624.
33. a) H.-J. Krüger in Biomimetic Oxidations Catalyzed by Metal Complexes (Ed.: B. Meunier), Imperial College Press, London, 2000;
34. b) P. E. M. Siegbahn, T. Borowski, Acc. Chem. Res. 2006, 39, 729738;
35. c) P. C. A. Bruijnincx, M. Lutz, A. L. Spek, W. R. Hagen, B. M. Weckhuysen, G. van Koten, R. J. M. Klein Gebbink, J. Am. Chem. Soc. 2007, 129, 2275-2286;
36. d) P. C. A. Bruijnincx, M. Lutz, A. L. Spek, W. R. Hagen, G. van Koten, R. J.. M. Klein Gebbink, Inorg. Chem. 2007, 46, 8391-8402.
37. H. G. Jang, D.D. Cox, L. Que, Jr., J. Am. Chem. Soc. 1991, 113, 9200-9204.
38. D. D. Cox, S. J. Benkovic, L. M. Bloom, F. C. Bradley, M. J. Nelson, L. Que Jr. , D. E. Wallick, J. Am. Chem. Soc. 1988, 110, 2026-2032.
39. 2 was confirmed by FT-IR (see the Supporting Information). The same complexes have been found highly robust under harsher autoxidation conditions with microwave assisted protocols see M. Bonchio, M. Carrara, G. Scorrano, U. Kortz, Adv. Synth. Catal. 2005, 347, 1909-1912.
40. 18 upon addition of 4-tert-butylcatechol and 4-chlorocatechol in DCE are at 729 nm (shoulder at 652) and 671 nm (shoulder at 622 nm), respectively.
41. D. D. Cox, L. Que, Jr., J. Am. Chem. Soc. 1988, 110, 8085-8092.
42. a) M. Pascaly, M. Duda, F. Schweppe, K. Zurlinden, F. K. Muller, B. Krebs, J. Chem. Soc. Dalton Trans. 2001, 828-837;
43. b) P. Mialane, L. Tchertanov, F. Banse, J. Sainton, J.-J. Girerd, Inorg. Chem. 2000, 39, 2440-2444.
44. 18 are reported in the Supporting Information. CCDC 724754, 724755, and 724756 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
45. A. Dolbecq, J.-D. Compain, P. Mialane, J. Marrot, E. Rivière, F. Sécheresse, Inorg. Chem. 2008, 47, 3371-3378.
46. 4 salt by cation metathesis, which offers an optimal synthetic strategy for tuning the solubility of the POM catalyst (Table S5 in the Supporting Information).
47. 2O 98:2 was reported to be an effective solvent for this reaction, see: T. Funabiki, I. Yoneda, M. Ishikawa, M. Ujiie, Y Nagai, S. Yoshida, J. Chem. Soc. Chem. Commun. 1994,1453.
48. 1H NMR exclude the formation of five-member ring 2pyrones. A non-regioselective cleavage is generally observed in abiotic systems. Computational arguments point at a subtle interplay of factors that might modulate the oxidative cleavage preference. See reference [21].
49. II lead to negligible DTBC conversion (<2%).
50. L. Que, Jr., R. C. Kolanczyk, L. S. White, J. Am. Chem Soc. 1987, 109, 5373-5380.
51. The pioneering work on transition-metal supported POMs is inspiring as this POM structural type displays cis-coordination sites, coordinative unsaturation, interesting reactivity and selectivity, see reference [19a] and H. Weiner, Y Hayashi, R. G. Finke, Inorg. Chem. 1999, 35, 2579-2591.