Regioselective alkene carbon-carbon bond cleavage to aldehydes and chemoselective alcohol oxidation of allylic alcohols with hydrogen peroxide catalyzed by [cis-Ru(II)(dmp)2(H2O)2] 2+ (dmp = 2,9-dimethylphenanthroline)

Organic Letters

Volumn 7, Issue 22, 2005, Pages 5039-5042

  Kogan, Vladimir ^a   Quintal, Miriam M ^a   Neumann, Ronny ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 27644509225     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052025e     Document Type: Article

References (38)

1. (a) Kühn, F. E.; Scherbaum, A.; Herrmann, W. A. J. Organomet. Chem. 2004, 689, 4149.
2. (b) Jost, C.; Wahl, G.; Kleinhenz, D.; Sundermeyer, J. Peroxide Chem. 2000, 341.
3. (c) Sanderson, W. R. Pure Appl. Chem. 2000, 72, 1289.
4. (d) Conte, V.; di Furia, F.; Licini, G. Appl. Catal., A 1997, 157, 335.
5. (e) Adam, W.; Mitchell, C. M.; Saha-Müller, C. R.; Weichold, O. Struct. Bonding 2000, 97, 237.
6. (a) McLain, J. L.; Lee, J.; Groves, J. T. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: London, 2000; pp 91.
7. (b) Meunier, B. Chem. Rev. 1992, 92, 1411.
8. (c) Brinksma, J.; de Boer, J. W.; Hage, R.; Feringa, B. L. Modern Oxidation Methods; Bäckvall, J. E., Ed.; Wiley-VCH: Weinheim, Germany, 2004; p 295.
9. (a) Sica, D. Recent Res. Dev. Org. Chem 2003, 7, 105.
10. (b) Courtney, J. L. Organic Synthesis and Oxidation with Metal Compounds; Mijs, W. J., Cornelis, R. H. I., Eds.; Plenum: New York, 1986; p 445.
11. Travis, B. R.; Narayan, R. S.; Borhan, B. J. Am. Chem. Soc. 2002, 124, 3824-3825.
12. (a) Antonelli, E.; D'Aloisio, R.; Gambaro, M.; Fiorani, T.; Venurello, C. J. Org. Chem. 1998, 63, 7190.
13. (b) Haimov, A.; Cohen, H.; Neumann, R. J. Am. Chem. Soc. 2004, 126, 11762.
14. (a) Beller, M.; Sharpless, K. B. Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed.; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Vol. 3, p 1149.
15. (b) Donohoe, T. J. Synlettt 2002, 1223.
16. (c) Severeyns, A.; de Vos, D. E.; Jacobs, P. A. Top. Catal. 2002, 19, 125.
17. (d) Sundermeier, U.; Döbler, C.; Beller, M. Modern Oxidation Methods; Bäckvall, J. E., Ed.; Wiley-VCH: Weinheim, Germany, 2004; p 1.
18. (a) Brinksma, J.; Schmieder, L.; van Vleit, G.; Boaron, R.; Hage, R.; de Vos, D. E.; Alsters, P. L.; Feringa, B. L. Tetrahedron Lett. 2002, 43, 2619.
19. (b) de Vos, D. E.; de Wildeman, S.; Sels, B. F.; Grobet, P. J.; Jacobs, P. A. Angew. Chem., Int. Ed. 1999, 38, 980.
20. (c) Fujita, M.; Costas, M.; Que, L. J. Am. Chem. Soc. 2003, 125, 9912.
21. (d) Costas, M.; Que, L. Angew. Chem., Int. Ed. 2002, 41, 2179.
22. (e) Ryu, J. Y.; Kim, J.; Costas, M.; Chen, K.; Nam, W.; Que, L. Chem. Commun. 2002, 1288.
23. (f) Costas, M.; Tipton, A. K.; Chen, K.; Jo, D. H.; Que, L. J. Am. Chem. Soc. 2001, 123, 6722.
24. (g) Herrmann, W. A.; Marz, D.; Herdtweck, E.; Schäfer, A.; Wagner, W.; Kneuper, H.-J. Angew. Chem., Int. Ed. Engl. 1987, 26, 462.
25. (h) Shing, T. K. M.; Tai, V. W.-F.; Tam, E. K. W. Angew. Chem., Int. Ed. Engl. 1994, 33, 2312.
26. (i) Shing, T. K. M.; Tam, E. K. W.; Tai, V. W.-F.; Chung, I. H. F.; Jiang, Q. Chem. Eur. J. 1996, 2, 50.
27. (a) Suslick, K. S.; Cook, B. R. J. Chem. Soc., Chem. Commun. 1987, 200.
28. (b) Ahn, K. H.; Groves, J. T. Bull. Korean Chem. Soc. 1994, 15, 957.
29. (c) Lai, T.; Lee, S. K.; Yeung, L.; Liu, H.; Williams, I. D.; Chang, C. K. Chem. Commun. 2003, 620. 7
30. (d) Kamata, K.; Nakagawa, Y.; Yamaguchi, K.; Mizuno, N. J. Catal. 2004, 224, 224. 7
31. (e) Groves, J. T.; Neumann, R. J. Am. Chem. Soc. 1987, 109, 5045.
32. (a) Goldstein, A. S.; Beer, R. H.; Drago, R. S. J. Am. Chem. Soc. 1994, 116, 2424.
33. (b) Goldstein, A. S.; Drago, R. S. J. Chem. Soc., Chem. Commun. 1991, 218.
34. (c) Bailey, C. L.; Drago, R. S. J. Chem. Soc., Chem. Commun. 1987, 179.
35. Collin, J. P.; Sauvage, J. P. Inorg. Chem. 1986, 25, 135.
36. 6 counteranion.
37. 2]. Peaks attributable to the molecular clusters were observed at m/z = 559 and 550, respectively.
38. Arends, I. W. C. E.; Sheldon, R. A. Modern Oxidation Methods; Bäckvall, J. E., Ed.; Wiley-VCH: Weinheim, Germany, 2004; p 83.