Catalytic photooxidation of 4-methoxybenzyl alcohol with a flavin-zinc(n)-cyclen complex

Chemistry - A European Journal

Volumn 10, Issue 24, 2004, Pages 6223-6231

  Cibulka, Radek ^a   Vasold, Rudolf ^b   König, Burkhard ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Electron transfer; Flavin; Macrocyclic ligands; Photooxidation; Sensitizers

Indexed keywords

ACETONITRILE; CATALYSIS; CHEMICAL BONDS; CHROMOPHORES; COMPLEXATION; CONCENTRATION (PROCESS); IRRADIATION; MOLECULAR STRUCTURE; PHOTOOXIDATION; SUBSTRATES;

BENZYL ALCOHOLS; COVALENTLY LINKED SUBSTRATES; FLAVIN; REOXIDIZED ALCOHOLS;

ALCOHOLS;

4 METHOXYBENZYL ALCOHOL; ACETONITRILE; ALCOHOL DERIVATIVE; BENZALDEHYDE; QUERCETIN; UNCLASSIFIED DRUG; ZINC COMPLEX;

ARTICLE; BINDING SITE; CATALYSIS; CHROMATOPHORE; COMPLEX FORMATION; COVALENT BOND; ELECTRON TRANSPORT; OXIDATION KINETICS; PHOTOCHEMISTRY; PHOTOOXIDATION; QUANTUM YIELD; RADIATION EXPOSURE;

EID: 10944263865     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400232     Document Type: Article

References (85)

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29. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
30. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
31. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
32. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
33. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
34. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
35. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
36. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
37. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
38. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
39. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
40. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
41. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
42. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
43. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
44. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
45. Examples of alcohol oxidations catalyzed by metal ion complexes: a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046; b) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540; c) G-J. ten Bring, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639; d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc 1997, 119, 12 661-12 662; e) P. Chaudhuri, M. Hess, T. Weyhermüller, K. Wieghardt, Angew. Chem. 1999, 111, 1165-1168; Angew. Chem. Int. Ed. 1999, 38, 1095-1098; f) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833; g) G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662; h) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720-4724; Angew. Chem. Int. Ed. 2002, 41, 4538-4542; i) Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197; j) P. Chaudhuri, M. Hess, J Müller, K. Hildenbrand, E. Bill, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc. 1999, 121, 9599-9610; k) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625; l) G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991; m) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catalysis Today, 2000, 57, 157-166; n) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2004, 346, 109-119.
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