Efficient catalytic cycloalkane oxidation employing a "helmet" phthalocyaninato iron(III) complex

Dalton Transactions

Volumn 40, Issue 22, 2011, Pages 5921-5925

  Brown, Elizabeth S ^a   Robinson, Jerome R ^a   McCoy, Aaron M ^a   McGaff, Robert W ^a  

^a UNIVERSITY OF WISCONSIN LA CROSSE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC ACTIVITY; CYCLOHEXANOL; CYCLOOCTANE OXIDATION; CYCLOOCTANES; INERT ATMOSPHERES; OXIDATION OF CYCLOHEXANE; OXIDATION REACTIONS; PRODUCT MIXTURE; SELECTIVE CATALYSTS; TURNOVER NUMBER;

CATALYST ACTIVITY; CATALYST SELECTIVITY; CYCLOHEXANE; HYDROGEN; HYDROGEN PEROXIDE; IRON COMPOUNDS; KETONES; ORGANIC COMPOUNDS; OXIDATION;

CATALYTIC OXIDATION;

EID: 79957673059     PISSN: 14779226     EISSN: 14779234     Source Type: Journal    
DOI: 10.1039/c1dt10147a     Document Type: Article

References (44)

1. C. D. Molek J. A. Halfen J. C. Loe R. W. McGaff Chem. Commun. 2001 2644
2. H. M. Kieler M. J. Bierman I. A. Guzei P. J. Liska R. W. McGaff Chem. Commun. 2006 3326
3. For monographs reviewing the general subject of phthalocyanines, their properties, and applications see, for example: N. B. McKeown, Phthalocyanine Materials: Synthesis Structure and Function, Cambridge University Press, Cambridge, 1998
4. J. Obirai F. Bedioui T. Nyokong J. Electroanal. Chem. 2005 576 323
5. B. Agboola K. I. Ozoemena T. Nyokong J. Mol. Catal. A: Chem. 2005 227 209
6. N. Sehlotho T. Nyokong J. Mol. Catal. A: Chem. 2004 209 51
7. S.-I. Murahashi X.-G. Zhou N. Komiya Synlett 2003 321
8. A. B. Sorokin S. Mangematin C. Pergrale J. Mol. Catal. A: Chem. 2002 182 267
9. N. Grootboom T. Nyokong J. Mol. Catal. A: Chem. 2002 179 113
10. H. M. Li H. M. Shu X. K. Ye Y. Wu Prog. Chem. 2001 13 461
11. A. B. Sorokin A. Tuel Catal. Today 2000 57 45
12. M. Bressan N. Celli N. d'Alessandro L. Liberatore A. Morvillo L. Tonucci J. Organomet. Chem. 2000 593 416
13. N. S. Zefirov A. N. Zakharov Can. J. Chem. 1998 76 955
14. A. Sorokin B. Meunier Eur. J. Inorg. Chem. 1998 1269
15. T. Schmidt W. Hartung F. Wasgestian Inorg. Chim. Acta 1998 274 126
16. M. Alvaro E. Carbonell M. Esplá H. Garcia Appl. Catal., B 2005 57 37
17. B. Meunier A. Sorokin Acc. Chem. Res. 1997 30 470
18. A. B. Sorokin F. Quignard R. Valentin S. Mangematin Appl. Catal., A 2006 309 162
19. C. Pérrolier A. B. Sorokin Chem. Commun. 2002 1548
20. A. B. Sorokin A. Tuel New J. Chem. 1999 23 473
21. A. Shaabani E. Farhangi A. Rahmati Appl. Catal., A 2008 338 14
22. P. Comba S. Wunderlich Chem. Eur. J. 2010 16 7293
23. P. Comba M. Maurer P. Vadivelu Inorg. Chem. 2009 48 10389
24. G. Roelfes M. Lubben R. Hage L. Que Jr. B. L. Feringa Chem.-Eur. J. 2000 6 2152
25. G. Bilis K. C. Christoforidis Y. Deligiannakis M. Louloudi Catal. Today 2010 157 101
26. P. Comba M. Maurer P. Vadivelu J. Phys. Chem. A 2008 112 13028
27. B. Retcher J. S. Costa J. Tang R. Hage P. Gamez J. Reedijk J. Mol. Catal. A: Chem. 2008 286 1
28. M. S. Chen M. C. White Science 2007 318 783
29. F. Li M. Wang C. Ma A. Gao H. Chen L. Sun Dalton Trans. 2006 2427
30. K. Chen M. Costas L. Que, Jr. J. Chem. Soc., Dalton Trans. 2002 672
31. K. Chen L. Que, Jr. J. Am. Chem. Soc. 2001 123 6327
32. P. A. MacFaul K. U. Ingold D. D. M. Wayner L. Que, Jr. J. Am. Chem. Soc. 1997 119 10594
33. S. Tanase E. Bouwman Adv. Inorg. Chem. 2006 58 29
34. L. Que Jr. R. Y. N. Ho Chem. Rev. 1996 96 2607
35. M. Costas M. P. Mehn M. P. Jensen L. Que, Jr. Chem. Rev. 2004 104 939
36. W. Nam Acc. Chem. Res. 2007 40 522
37. B. Meunier, Biomimetic Oxidations Catalyzed by Transition Metal Complexes, Imperial College Press, London, 2000
38. F. Mei C. Ou G. Wu L. Cao F. Han X. Meng J. Li D. Li Z. Liao Dalton Trans. 2010 39 4267
39. B. Meunier Chem. Rev. 1992 92 1411
40. A. E. Shilov G. B. Shul'pin Chem. Rev. 1997 97 2879
41. S.-I. Murahashi Angew. Chem., Int. Ed. Engl. 1995 34 2443
42. The pre-catalyst 1 used in this study is prepared in crystalline form, where the composition of the crystals can vary slightly. In the crystallographically determined structure (Ref. 2), ligand L is observed to be a mixture of methanol and water, with two co-crystallized methanol molecules also being present for every complex bearing a methanol ligand, whereas three co-crystallized methanol molecules are present for every complex bearing a water ligand. In a desire to report catalyst performance conservatively in light of this issue, we have calculated TON values based on an assumption that the pre-catalyst has 100% methanol as the L ligand, which along with the two co-crystallized methanol molecules gives a formula weight of 806.65, less than that for the case where L = water and three co-crystallized methanol molecules are present, in which case the formula weight is 824.66. This results in slightly under-reported turnover numbers, assuming a mixture of the two species is actually present, because the number of moles of catalyst actually present in the reaction mixtures will be very slightly less than the number used in TON calculations
43. J. T. Groves T. E. Nemo J. Am. Chem. Soc. 1983 105 6243
44. W. Nam Y. M. Goh Y. J. Lee M. H. Lim C. Kim Inorg. Chem. 1999 38 3238