Aerobic oxidation of cycloalkanes, alcohols and ethylbenzene catalyzed by the novel carbon radical chain promoter NHS (N-hydroxysaccharin)

Advanced Synthesis and Catalysis

Volumn 346, Issue 2-3, 2004, Pages 286-296

  Baucherel, Xavier ^a,b   Gonsalvi, Luca ^a,c   Arends, Isabel W C E ^a   Ellwood, Simon ^d   Sheldon, Roger A ^a  

^a DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b JOHNSON MATTHEY CATALYSTS   (United Kingdom)

^c Area di Ricerca CNR di Firenze   (Italy)

^d Givaudan SA   (Switzerland)

Author keywords

Alcohols; C H activation; Cycloalkanes; Molecular oxygen; Oxidation

Indexed keywords

ALCOHOL; CARBON; CYCLOALKANE; ETHYLBENZENE; SACCHARIN DERIVATIVE;

ADDITION REACTION; ALCOHOL OXIDATION; ARTICLE; AUTOOXIDATION; CATALYSIS; COMPETITION; CYCLOADDITION; DECOMPOSITION; DISSOCIATION; OXIDATION KINETICS; REACTION ANALYSIS; TEMPERATURE;

EID: 1942535077     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303197     Document Type: Article

References (38)

1. a) R. A. Sheldon, J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981;
2. b) C. L. Hill, Activation and Functionalization of Alkanes, Academic Press, New York, 1989.
3. a) Y. Ishii, T. Iwahama, S. Sakaguchi, K. Nakayama, M. Takeno, Y. Nishiyama, J. Org. Chem. 1996, 61, 4520-4526;
4. b) Y. Ishii, J. Mol. Catal. A: Chem. 1997, 117, 123-137;
5. c) Y Ishii, S. Sakaguchi, Catalysis Surveys from Japan 1999, 3, 27-35;
6. d) Y. Ishii, Eur. Patent EP 0 824 962 A1, 1996;
7. e) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal. 2001, 343, 393-427.
8. B. B. Wentzel, M. P. J. Donners, P. L. Alsters, M. C. Feiters, R. J. M. Nolte, Tetrahedron 2000, 56, 7797-7803.
9. K. Gorgy, J-C. Lepretre, E. Saint-Aman, C. Einhorn, J. Einhorn, C. Marcadal, J.-L. Pierre, Electrochim. Acta 1998, 44, 385-393.
10. H. T. Nagasawa, S. P. Kawle, J. A. Elberling, E. G. De-Master, J. M. Fukuto, J. Med. Chem. 1995, 38, 1865-1871.
11. N. Hirai, N. Sawatari, N. Nakamura, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2003, 68, 6587-6590.
12. a) X. Baucherel, I. W. C. E. Arends, S. Ellwood, R. A. Sheldon, Org. Proc. Res. Dev. 2003, 7, 426-428;
13. b) X. Baucherel, R. A. Sheldon, WO 02100810, 2002.
14. I. W. C. E. Arends, M. Sasidharan, A. Kuehnle, M. Duda, C. Jost, R. A. Sheldon, Tetrahedron 2002, 58, 9055-9061.
15. A. Onopchenko, J. G. D. Schulz, J. Org. Chem. 1973, 38, 3729.
16. W. Partenheimer, J. Mol. Catal. A: Chemical 2001, 174, 29-33.
17. W. Partenheimer, J. Mol. Catal. A: Chemical 2003, 206, 105-119.
18. J. Muzart, Chem. Rev. 1992, 92, 113-140.
19. a) T. Welton, Chem. Rev. 1999, 99, 2071-2084;
20. b) R. A. Sheldon, Chem. Commun. 2001, 2399-2407.
21. K. Matsunaka, T. Iwahama, S. Sakaguchi, Y. Ishii, Tetrahedron Lett. 1999, 40, 2165-2168.
22. a) S. Wilsey, P. Dowd, K. N. Houk, J. Org. Chem. 1999, 64, 8801;
23. b) A. L. J. Beckwith, B. P. Hay, J. Am. Chem. Soc. 1989, 111, 2674((+ Kochi ??)).
24. 2, see: h) T. Nishimura, K. Ohe, S. J. Uemura, J. Am. Chem. Soc. 1999, 121, 2645; i) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355; for methods based on Cu, see: j) I. E. Marko, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, A. Gautier, S. M. Brown, C. J. Urch, J. Org. Chem., 1999, 64, 2433; k) B. Betzemeier, M. Cavazzine, S. Quici, P. Knochel, P. Tetrahedron Lett. 2000, 41, 4343; l) P. Gamez, I. W. C. E. Arends, J. Reedijk, R. A. Sheldon, Chem. Commun. 2003, 2414.
25. 2, see: h) T. Nishimura, K. Ohe, S. J. Uemura, J. Am. Chem. Soc. 1999, 121, 2645; i) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355; for methods based on Cu, see: j) I. E. Marko, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, A. Gautier, S. M. Brown, C. J. Urch, J. Org. Chem., 1999, 64, 2433; k) B. Betzemeier, M. Cavazzine, S. Quici, P. Knochel, P. Tetrahedron Lett. 2000, 41, 4343; l) P. Gamez, I. W. C. E. Arends, J. Reedijk, R. A. Sheldon, Chem. Commun. 2003, 2414.
26. 2, see: h) T. Nishimura, K. Ohe, S. J. Uemura, J. Am. Chem. Soc. 1999, 121, 2645; i) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355; for methods based on Cu, see: j) I. E. Marko, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, A. Gautier, S. M. Brown, C. J. Urch, J. Org. Chem., 1999, 64, 2433; k) B. Betzemeier, M. Cavazzine, S. Quici, P. Knochel, P. Tetrahedron Lett. 2000, 41, 4343; l) P. Gamez, I. W. C. E. Arends, J. Reedijk, R. A. Sheldon, Chem. Commun. 2003, 2414.
27. 2, see: h) T. Nishimura, K. Ohe, S. J. Uemura, J. Am. Chem. Soc. 1999, 121, 2645; i) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355; for methods based on Cu, see: j) I. E. Marko, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, A. Gautier, S. M. Brown, C. J. Urch, J. Org. Chem., 1999, 64, 2433; k) B. Betzemeier, M. Cavazzine, S. Quici, P. Knochel, P. Tetrahedron Lett. 2000, 41, 4343; l) P. Gamez, I. W. C. E. Arends, J. Reedijk, R. A. Sheldon, Chem. Commun. 2003, 2414.
28. 2, see: h) T. Nishimura, K. Ohe, S. J. Uemura, J. Am. Chem. Soc. 1999, 121, 2645; i) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355; for methods based on Cu, see: j) I. E. Marko, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, A. Gautier, S. M. Brown, C. J. Urch, J. Org. Chem., 1999, 64, 2433; k) B. Betzemeier, M. Cavazzine, S. Quici, P. Knochel, P. Tetrahedron Lett. 2000, 41, 4343; l) P. Gamez, I. W. C. E. Arends, J. Reedijk, R. A. Sheldon, Chem. Commun. 2003, 2414.
29. 2, see: h) T. Nishimura, K. Ohe, S. J. Uemura, J. Am. Chem. Soc. 1999, 121, 2645; i) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355; for methods based on Cu, see: j) I. E. Marko, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, A. Gautier, S. M. Brown, C. J. Urch, J. Org. Chem., 1999, 64, 2433; k) B. Betzemeier, M. Cavazzine, S. Quici, P. Knochel, P. Tetrahedron Lett. 2000, 41, 4343; l) P. Gamez, I. W. C. E. Arends, J. Reedijk, R. A. Sheldon, Chem. Commun. 2003, 2414.
30. 2, see: h) T. Nishimura, K. Ohe, S. J. Uemura, J. Am. Chem. Soc. 1999, 121, 2645; i) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355; for methods based on Cu, see: j) I. E. Marko, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, A. Gautier, S. M. Brown, C. J. Urch, J. Org. Chem., 1999, 64, 2433; k) B. Betzemeier, M. Cavazzine, S. Quici, P. Knochel, P. Tetrahedron Lett. 2000, 41, 4343; l) P. Gamez, I. W. C. E. Arends, J. Reedijk, R. A. Sheldon, Chem. Commun. 2003, 2414.
31. 2, see: h) T. Nishimura, K. Ohe, S. J. Uemura, J. Am. Chem. Soc. 1999, 121, 2645; i) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355; for methods based on Cu, see: j) I. E. Marko, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, A. Gautier, S. M. Brown, C. J. Urch, J. Org. Chem., 1999, 64, 2433; k) B. Betzemeier, M. Cavazzine, S. Quici, P. Knochel, P. Tetrahedron Lett. 2000, 41, 4343; l) P. Gamez, I. W. C. E. Arends, J. Reedijk, R. A. Sheldon, Chem. Commun. 2003, 2414.
32. 2, see: h) T. Nishimura, K. Ohe, S. J. Uemura, J. Am. Chem. Soc. 1999, 121, 2645; i) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355; for methods based on Cu, see: j) I. E. Marko, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, A. Gautier, S. M. Brown, C. J. Urch, J. Org. Chem., 1999, 64, 2433; k) B. Betzemeier, M. Cavazzine, S. Quici, P. Knochel, P. Tetrahedron Lett. 2000, 41, 4343; l) P. Gamez, I. W. C. E. Arends, J. Reedijk, R. A. Sheldon, Chem. Commun. 2003, 2414.
33. 2, see: h) T. Nishimura, K. Ohe, S. J. Uemura, J. Am. Chem. Soc. 1999, 121, 2645; i) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355; for methods based on Cu, see: j) I. E. Marko, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, A. Gautier, S. M. Brown, C. J. Urch, J. Org. Chem., 1999, 64, 2433; k) B. Betzemeier, M. Cavazzine, S. Quici, P. Knochel, P. Tetrahedron Lett. 2000, 41, 4343; l) P. Gamez, I. W. C. E. Arends, J. Reedijk, R. A. Sheldon, Chem. Commun. 2003, 2414.
34. 2, see: h) T. Nishimura, K. Ohe, S. J. Uemura, J. Am. Chem. Soc. 1999, 121, 2645; i) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355; for methods based on Cu, see: j) I. E. Marko, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, A. Gautier, S. M. Brown, C. J. Urch, J. Org. Chem., 1999, 64, 2433; k) B. Betzemeier, M. Cavazzine, S. Quici, P. Knochel, P. Tetrahedron Lett. 2000, 41, 4343; l) P. Gamez, I. W. C. E. Arends, J. Reedijk, R. A. Sheldon, Chem. Commun. 2003, 2414.
35. 2, see: h) T. Nishimura, K. Ohe, S. J. Uemura, J. Am. Chem. Soc. 1999, 121, 2645; i) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355; for methods based on Cu, see: j) I. E. Marko, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, A. Gautier, S. M. Brown, C. J. Urch, J. Org. Chem., 1999, 64, 2433; k) B. Betzemeier, M. Cavazzine, S. Quici, P. Knochel, P. Tetrahedron Lett. 2000, 41, 4343; l) P. Gamez, I. W. C. E. Arends, J. Reedijk, R. A. Sheldon, Chem. Commun. 2003, 2414.
36. T. Iwahama, S. Sakaguchi, Y. Nishiyama, Y. Ishii, Tetrahedron Lett. 1995, 36, 6923-6926.
37. T. Iwahama, Y. Yoshino, T. Keitoku, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2000, 65, 6502-6507.
38. R. Amorati, M. Lucarini, V. Mugnaini, G. F. Pedulli, F. Minisci, F. Recupero, F. Fontana, P. Astolfi, L. Greci, J. Org. Chem. 2003, 68, 1747-1754.