Highly efficient, organocatalytic aerobic alcohol oxidation

Journal of the American Chemical Society

Volumn 133, Issue 17, 2011, Pages 6497-6500

  Shibuya, Masatoshi ^a   Osada, Yuji ^a   Sasano, Yusuke ^a   Tomizawa, Masaki ^a   Iwabuchi, Yoshiharu ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AEROBIC OXIDATIONS; ALCOHOL OXIDATION; AMBIENT PRESSURES; BI-FUNCTIONAL CATALYSTS; ORGANOCATALYTIC; SALT-FREE SYSTEM;

FLUORINE; ORGANIC POLYMERS; TRANSITION METALS;

CATALYTIC OXIDATION;

5 FLUORO 2 AZAADAMANTANE N OXYL; ALCOHOL; AMANTADINE DERIVATIVE; AMMONIA; HALOGEN; NITRIC OXIDE; OXOAMMONIUM NITRATE; RADICAL; UNCLASSIFIED DRUG;

AEROBIC CAPACITY; ALCOHOL OXIDATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; ENVIRONMENTAL TEMPERATURE; OXIDATION; OXYGENATION; PRESSURE;

ADAMANTANE; ALCOHOLS; CATALYSIS; CYCLIC N-OXIDES; OXIDATION-REDUCTION;

EID: 79955456942     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja110940c     Document Type: Article

References (52)

1. Caron, S.; Dugger, R. W.; Ruggeri, S. G.; Ragan, J. A.; Brown Ripin, D. H. Chem. Rev. 2006, 106, 2943-2989
2. Dugger, R. W.; Ragan, J. A.; Brown Ripin, D. H. Org. Process Res. Dev. 2005, 9, 253-258
3. Modern Oxidation Methods; Bäckvall, J.-E., Ed.; Wiley-VCH: Weinheim, Germany, 2004.
4. Schultz, M. J.; Sigman, M. S. Tetrahedron 2006, 62, 8227-8241
5. Sheldon, R. A.; Arends, I. W. C. E. J. Mol. Catal. A.: Chem. 2006, 251, 200-214
6. Sheldon, R. A.; Arends, I. W. C. E. Adv. Synth. Catal. 2004, 346, 1051-1071
7. Sheldon, R. A.; Arends, I. W. C. E.; ten Brink, G.-J.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774-781
8. ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636-1639
9. Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M.; Urch, C. J. Science 1996, 274, 2044-2046
10. Lenoir, D. Angew. Chem., Int. Ed. 2006, 45, 3206-3210
11. Shibuya, M.; Sato, T.; Tomizawa, M.; Iwabuchi, Y. Chem. Commun. 2009, 1739-1741
12. Shibuya, M.; Tomizawa, M.; Suzuki, I.; Iwabuchi, Y. J. Am. Chem. Soc. 2006, 128, 8412-8413
13. Liu, R.; Liang, X.; Dong, C.; Hu, X. J. Am. Chem. Soc. 2004, 126, 4112-4113
14. He, X.; Shen, Z.; Mo, W.; Sun, N.; Hu, B.; Hu, X. Adv. Synth. Catal. 2009, 351, 89-92
15. Wang, X.; Liu, R.; Jin, Y.; Liang, X. Chem.-Eur. J. 2008, 14, 2679-2685
16. Xie, Y.; Mo, W.; Xu, D.; Shen, Z.; Sun, N.; Hu, B.; Hu, X. J. Org. Chem. 2007, 72, 4288-4291
17. Wang, N.; Liu, R.; Chen, J.; Liang, X. Chem. Commun. 2005, 5322-5324
18. Liu, R.; Dong, C.; Liang, X.; Wang, X.; Hu, X. J. Org. Chem. 2005, 70, 729-731
19. Bobbitt, J. M.; Bruckner, C.; Merbouh, N. Org. React. 2009, 74, 103-424
20. Vogler, T.; Studer, A. Synthesis 2008, 1979-1993
21. de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153-1174
22. Anelli, P. L.; Banfi, S.; Montanari, F.; Quici, S. J. Org. Chem. 1989, 54, 2970-2972
23. Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559-2562
24. De Mico, A.; Margarita, R.; Parlanti, L.; Vescovi, A.; Piancatelli, G. J. Org. Chem. 1997, 62, 6974-6977
25. Uyanik, M.; Fukatsu, R.; Ishihara, K. Chem.-Asian. J. 2010, 5, 456-460
26. Shibuya, M.; Tomizawa, M.; Sasano, Y.; Iwabuchi, Y. J. Org. Chem. 2009, 74, 4619-4622
27. Demizu, Y.; Shiigi, H.; Oda, T.; Matsumura, Y.; Onomura, O. Tetrahedron Lett. 2008, 49, 48-52
28. 2.
29. 2 decreases because of the increasing oxidation potential.
30. Chou, S.; Nelson, J. A.; Spencer, T. A. J. Org. Chem. 1974, 39, 2356-2361
31. - by ion chromatography.
32. In DSC analysis, the starting point of exothermic decomposition was 116 °C, and the amount of heat released was 1815 J/g. These data do not suggest the necessity of careful operation involving 11 to prevent explosion in laboratory-scale operation. (34)
33. 9 was easily prepared from 2-azaadamantane by a five-step method that we have established as a kilogram-scale preparation procedure (WO 2009/066735). (34)
34. 2, and 5 mol % 11 realized the aerobic oxidation under AcOH-free conditions. (34)
35. 2 gas. (34)
36. 11 was stable enough to handle in air.
37. Yamakoshi, H.; Shibuya, M.; Tomizawa, M.; Osada, Y.; Kanoh, N.; Iwabuchi, Y. Org. Lett. 2010, 12, 980-983
38. Tu, Y.; Frohn, M.; Wang, Z.-X.; Shi, Y. Org. Synth. 2003, 80, 1-8
39. Gonsalvi, L.; Arends, I. W. C. E.; Sheldon, R. A. Org. Lett. 2002, 4, 1659-1661
40. In accordance with the comment of one of the reviewers, we attempted the 0.1 mol scale oxidation of 1,2:4,5-di- O -isopropylidene-β- d -fructopyranose (22a). Because of an efficient electron transfer system, the reaction proceeded smoothly to give the product in high yield without pressurized oxygen. (34)
41. Hattori, H.; Nozawa, E.; Iino, T.; Yoshimura, Y.; Shuto, S.; Shimamoto, Y; Nomura, M.; Fukushima, M.; Tanaka, M.; Sasaki, T.; Matsuda, A. J. Med. Chem. 1998, 41, 2892-2902
42. Yoshimura, Y.; Sano, T.; Matsuda, A.; Ueda, T. Chem. Pharm. Bull. 1988, 36, 162-167
43. Appell, R. B.; Duguid, R. J. Org. Process Res. Dev. 2000, 4, 172-174
44. Azuma, A.; Nakajima, Y.; Nishizono, N.; Minakawa, N.; Suzuki, M.; Hanaoka, K.; Kobayashi, T.; Tanaka, M.; Sasaki, T.; Matsuda, A. J. Med. Chem. 1993, 36, 4183-4189
45. Matsuda, A.; Takenuki, K.; Tanaka, M.; Sasaki, T.; Ueda, T. J. Med. Chem. 1991, 34, 812-819
46. The use of AcOH as a solvent did not promote racemization either. MeCN gave the corresponding aldehyde in higher yield.
47. Pradhan, P. P.; Bobbitt, J. M.; Bailey, W. F. Org. Lett. 2006, 8, 5485-5487
48. 2 conditions. Metal-salt-free conditions promoted the production of 11.
49. The details are provided in the Supporting Information.
50. Rychnovsky, S. D.; Vaidyanathan, R.; Beauchamp, T.; Lin, R.; Farmer, P. J. J. Org. Chem. 1999, 64, 6745-6749
51. Bobbitt, J. M.; Flores, M. C. L. Heterocycles 1988, 27, 509-533
52. The reference electrode was Ag/AgCl.