A reasonable explanation for the mechanism of photo-promoted chemoselective aerobic oxidation of alcohols using (ON)Ru(salen) complex as catalyst

Tetrahedron Letters

Volumn 46, Issue 36, 2005, Pages 6049-6052

  Egami, Hiromichi ^a   Onitsuka, Satoaki ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

(ON)Ru(salen) complex; Aerobic oxidation; Intramolecular hydrogen atom transfer

Indexed keywords

ALCOHOL; HYDROGEN; ISOTOPE; LIGAND; RUTHENIUM COMPLEX;

ALCOHOL OXIDATION; ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; EXAMINATION; IRRADIATION; MOLECULAR MECHANICS; PHOTOCHEMISTRY; PROTON TRANSPORT;

EID: 23244450157     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.005     Document Type: Article

References (43)

1. S.V. Ley, and A. Madin B.M. Trost I. Fleming S.V. Ley Comprehensive Organic Synthesis Vol. 7 1991 Pergamon Press Oxford 251 289
2. T.V. Lee B.M. Trost I. Fleming S.V. Ley Comprehensive Organic Synthesis Vol. 7 1991 Pergamon Press Oxford 291 303
3. G. Procter B.M. Trost I. Fleming S.V. Ley Comprehensive Organic Synthesis Vol. 7 1991 Pergamon Press Oxford 305 327
4. For non-aerobic highly chemoselective oxidation of primary alcohols, H. Tomioka, K. Takai, K. Oshima, and H. Nozaki Tetrahedron Lett. 22 1981 1605 1608
5. E. Saint-Arnan, S. Menage, J.-L. Pierre, E. Defrancq, and G. Gellon New J. Chem. 1998 393
6. L.D. Luca, G. Giacomelli, and A. Porcheddu Org. Lett. 3 2001 3041
7. J. Matsuo, D. Iida, H. Yamanaka, and T. Mukaiyama Tetrahedron 59 2003 6739
8. R.A. Sheldon, and I.W.C.E. Arends L.I. Simandi Advances in Catalytic Activation of Dioxygen by Metal Complexes 2003 Kluwer Academic Dordrecht 123
9. T. Nishimura, T. Onoue, K. Ohe, and S. Uemura J. Org. Chem. 64 1999 6750 6755
10. I.-E. Markó, P.-R. Giles, M. Tsukazaki, S.-M. Brown, and C.-J. Urch Science 274 1996 2044 2046
11. B.M. Stolz Chem. Lett. 33 2004 362 367
12. R. Irie, and T. Katsuki Chem. Rec. 4 2004 96 109
13. A. Hanyu, E. Takezawa, S. Sakaguchi, and Y. Ishii Tetrahedron Lett. 39 1998 5557 5560
14. M.F. Semmelhack, C.R. Schmid, D.A. Cortes, and C.S. Chou J. Am. Chem. Soc. 106 1984 3374 3376
15. P. Gamez, I.W.C.E. Arends, J. Reedijk, and R.A. Sheldon Chem. Commun. 2003 2414 2425
16. K.-M. Choi, T. Akita, T. Mizugaki, K. Ebitani, and K. Kaneda New J. Chem. 27 2003 324 328
17. M. Hasan, M. Musawir, P.N. Davey, and I.V. Kozhevnikov J. Mol. Catal. A 180 2002 77 84
18. C.Y. Lorber, S.P. Smidt, and J.A. Osborn Eur. J. Inorg. Chem. 2000 655 658
19. K. Ebitani, Y. Fujie, and K. Kaneda Langmuir 15 1999 3557 3562
20. B. Hinzen, R. Lenz, and S.V. Ley Synthesis 1998 977 979
21. K. Kaneda, Y. Fujie, and K. Ebitani Tetrahedron Lett. 38 1997 9023 9026
22. X. Liu, A. Qiu, and D.T. Sawyer J. Am. Chem. Soc. 115 1993 3239 3243
23. C. Bilgrien, S. Davis, and R.J. Drago Am. Chem. Soc. 109 1997 3786 3787
24. M. Musawir, P.N. Davey, G. Kelly, and I.V. Kozhevnikov Chem. Commun. 2003 1414 1415
25. M. Matsumoto, and S. Ito J. Chem. Soc., Chem. Commun. 1981 907 908
26. M. Matsumoto, and N. Watanabe J. Org. Chem. 49 1984 3436 3437
27. Y. Uozumi, and R. Nakano Angew. Chem., Int. Ed. 42 2003 194 197
28. P. Gamez, I.W.C.E. Arends, J. Reedijk, and R.A. Sheldon Chem. Commun. 2003 2414 2415
29. A. Miyata, M. Murakami, R. Irie, and T. Katsuki Tetrahedron Lett. 42 2001 7067 7070
30. A. Miyata, M. Furukawa, R. Irie, and T. Katsuki Tetrahedron Lett. 43 2002 3481 3484
31. H. Egami, H. Shimizu, and T. Katsuki Tetrahedron Lett. 46 2005 783 786
32. A. Gaquere, S. Liang, F.-L. Hus, and X.R. Bu Tetrahedron: Asymmetry 13 2002 2089 2093
33. H. Shimizu, K. Nakata, and T. Katsuki Chem. Lett. 2002 1080 1081
34. H. Shimizu, and T. Katsuki Chem. Lett. 32 2003 480 481
35. H. Shimizu, S. Onitsuka, H. Egami, and T. Katsuki J. Am. Chem. Soc. 127 2005 5396 5413
36. For determination of the rate raws, see Ref. 7c: irradiation of a (nitrosyl)Ru(salen) complex in air gives the corresponding nitrosyl-free Ru(salen) complexes at the early stage of the oxidation under the conditions.
37. S.G. Minasian, M.M. Whittaker, and J.W. Whittaker Biochemistry 43 2004 13683 13693
38. R.C. Pratt, and T.D.P. Stack J. Am. Chem. Soc. 125 2003 8716 8717
39. M.M. Whittaker, and J.W. Whittaker Biochemistry 40 2001 7140 7148
40. Y. Wang, J.L. DuBois, B. Hedman, K.O. Hodgson, and T.D.P. Stack Science 279 1998 537 540
41. A. Dijksman, I.W.C.E. Arends, and R.A. Sheldon Org. Biomol. Chem. 1 2003 3232 3237
42. A similar mechanism including intramolecular hydrogen atom transfer has been proposed for Cu(II)-Schiff base-catalyzed aerobic oxidation of alcohols (Ref. 9d).
43. indep value may be too large, if only HAT contributes to the TS of the oxidation. This comment led us to an idea that the product might behave as a catalytic poison. The authors are grateful to him for this comment.