Environmentally benign oxidation reaction of benzylic and allylic alcohols to carbonyl compounds using Pd/C with sodium borohydride

Synlett

Volumn , Issue 1, 2007, Pages 95-98

  An, Gwangil ^a   Lim, Minkyung ^b   Chun, Kwon Soo ^a   Rhee, Hakjune ^b  

^a Korea Institute of Radiation and Medical Science   (South Korea)

^b Hanyang University   (South Korea)

Author keywords

Alcohols; Oxidations; Oxygen; Palladium; Sodium borohydride

Indexed keywords

ALCOHOL; ALCOHOL DERIVATIVE; ALLYL COMPOUND; BENZILIC ACID; CARBONYL DERIVATIVE; OXYGEN; PALLADIUM; POTASSIUM CARBONATE; REDUCING AGENT; SODIUM BOROHYDRIDE; SOLVENT;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ECONOMIC ASPECT; ENVIRONMENTAL FACTOR; OXIDATION; ROOM TEMPERATURE;

EID: 33846438239     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-956457     Document Type: Article

References (38)

1. (a) Sheldon, R. A.; Kochi, J. K. In Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1994.
2. (b) Hudlicky, M. In Oxidations in Organic Chemistry, ACS Monograph Series; American Chemical Society: Washington, DC, 1990.
3. For a list of methods, see: (a) Larock, R. C. In Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd ed.; John Wiley & Sons: New York, 1999, and references cited therein.
4. (b) Smith, M. B.; March, J. In March's Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 5th ed.; Wiley-Interscience: New York, 2001, and references cited therein.
5. (a) Mallat, T.; Baiker, A. Chem. Rev. 2004, 104, 3037.
6. (b) Kaneda, K.; Ebitani, K.; Mizugaki, T.; Mori, K. Bull. Chem. Soc. Jpn. 2006, 79, 981.
7. (c) Enache, D. I.; Edwards, J. K.; Landon, P.; Solsona-Espriu, B.; Carley, A. F.; Herzing, A. A.; Watanabe, M.; Kiely, C. J.; Knight, D. W.; Hutchings, G. J. Science 2006, 311, 362.
8. (d) Li, G.; Enache, D. I.; Edwards, J.; Carley, A. F.; Knight, D. W.; Hutchings, G. J. Catal. Lett. 2006, 110, 7.
9. (e) Maayan, G.; Ganchegui, B.; Leitner, W.; Neumann, R. Chem. Commun. 2006, 2230.
10. (f) Abad, A.; Almela, C.; Corma, A.; Garcia, H. Tetrahedron 2006, 62, 6666.
11. (g) Choudhary, V. R.; Dhar, A.; Jana, P.; Jha, R.; Uphade, B. S. Green Chem. 2005, 7, 768.
12. (h) Kwon, M. S.; Kim, N.; Park, C. M.; Lee, J. S.; Kang, K. Y.; Park, J. Org. Lett. 2005, 7, 1077.
13. (i) Tanaka, T.; Kawabata, H.; Hayashi, M. Tetrahedron Lett. 2005, 46, 4989.
14. (j) Caravati, M.; Grunwaldt, J.-D.; Baiker, A. Catal. Today 2004, 97-92, 1.
15. (k) Pillai, U. R.; Sahle-Demessie, E. Green Chem. 2004, 6, 161.
16. (a) Uozumi, Y.; Nakao, R. Angew. Chem. Int. Ed. 2003, 42, 194.
17. (b) Mori, K.; Yamaguchi, K.; Hara, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2002, 124, 11572.
18. (c) Kakiuchi, N.; Nishimura, T.; Inoue, M.; Uemura, S. Bull. Chem. Soc. Jpn. 2001, 74, 165.
19. (d) Nishimura, T.; Kakiuchi, N.; Inoue, M.; Uemura, S. Chem. Commun. 2000, 1245.
20. Luhring, P.; Schumpe, A. J. J. Chem. Eng. Data 1989, 34, 250.
21. Schultz, M. J.; Park, C. C.; Sigman, M. S. Chem. Commun. 2002, 3034.
22. (a) Besson, M.; Gallezot, P. Catal. Today 2000, 57, 127.
23. (b) Mallat, T.; Baiker, A. Catal. Today 1994, 19, 247.
24. (c) Heyns, K.; Paulsen, H. Adv. Carbohydr. Chem. 1962, 17, 169.
25. (d) Wieland, H. Ber. Dtsch. Chem. Ges. 1913, 46, 3327.
26. (a) Markusse, A. P.; Kuster, B. F. M.; Schouten, J. C. J. Mol. Catal. A: Chem. 2000, 158, 215.
27. (b) Markusse, A. P.; Kuster, B. F. M.; Koningsberger, D. C.; Marin, G. B. Catal. Lett. 1998, 55, 141.
28. (c) Vleeming, J. H.; Kuster, B. F. M.; Marin, G. B. Ind. Eng. Chem. Res. 1997, 36, 3541.
29. (d) Mallat, T.; Baiker, A.; Botz, L. Appl. Catal. A: Gen. 1992, 86, 147.
30. (e) Hendrix, H. E. J.; Kuster, B. F. M.; Marin, G. B. Carbohydr. Res. 1990, 204, 121.
31. (f) van Dam, H. E.; Wisse, L. J.; van Bekkum, H. Appl. Catal. 1990, 61, 187.
32. (g) Dijkgraaf, P. J. M.; Rijk, M. J. M.; Meuldijk, J.; van der Wiele, K. J. Catal. 1988, 112, 329.
33. (h) Dijkgraaf, P. J. M.; Duisters, H. A. M.; Kuster, B. F. M.; van der Wiele, K. J. Catal. 1988, 112, 337.
34. (i) van Dam, H. E.; Kiebom, A. P. G.; van Bekkum, H. Appl. Catal. 1987, 33, 361.
35. (j) van Dam, H. E.; Duijverman, P.; Kiebom, A. P. G.; van Bekkum, H. Appl. Catal. 1987, 33, 373.
36. (k) Smits, P. C. C.; Kuster, B. F. M.; van der Wiele, K.; van der Baan, H. S. Appl. Catal. 1987, 33, 83.
37. (l) Smits, P. C. C.; Kuster, B. F. M.; van der Wiele, K.; van der Baan, H. S. Carbohydr. Res. 1986, 153, 227.
38. 4, and concentrated via rotary evaporation. The residue was purified by silica gel flash column chromatography (EtOAc-n-hexane = 1:3-1:7). Reactions were typically run on a 2-3-mmol scale.