[RuCl2(p-cymene)]2 on carbon: An efficient, selective, reusable, and environmentally versatile heterogeneous catalyst

Organic Letters

Volumn 4, Issue 14, 2002, Pages 2369-2371

  Choi, Eunjung ^a   Lee, Chongmok ^a   Na, Youngim ^b   Chang, Sukbok ^b  

^a Ewha Womans University   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0013379360     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0260977     Document Type: Article

References (31)

1. For reviews, see: (a) Smith, K. Solid Supports and Catalysts in Organic Synthesis; Ellis Hornood: Chichester, 1992.
2. (b) Keim, W.; Driessen-Hölscher B. In Handbook of Heterogeneous Catalysis; Ertl, G., Knözinger, H., Weitkamp, J., Eds.; Wiley-VCH: Weinheim, 1997; Vol. 1, P 231.
3. (c) Basset, J. M.; Candy, J. P.; Santini, C. C. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 2, p 387.
4. (a) Blum, J.; Rosenfeld, A.; Polak, N.; Israelson, O.; Schumann, H.; Avnir, D. J. Mol. Catal. 1996, 107, 217.
5. (b) Herrmann, W. A.; Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1048.
6. (c) Thomas, J. M. Angew. Chem., Int. Ed. 1999, 38, 3588.
7. For some selected examples, see: (a) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 4147.
8. (b) Kobayashi, S.; Endo, M.; Nagayama, S. J. Am. Chem. Soc. 1999, 121, 11229.
9. (c) Son, S. U.; Lee, S. I.; Chung, Y. K. Angew. Chem., Int. Ed. 2000, 39, 4158.
10. (d) Yu, X.-Q.; Huang, J.-S.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2000, 122, 5337.
11. (e) Djakovitch, L.; Koehler, K. J. Am. Chem. Soc. 2001, 123, 5990.
12. (a) Na, Y.; Chang, S. Org. Lett. 2000, 2, 1887.
13. (b) Lee, M.; Chang, S. Tetrahedron Lett. 2000, 41, 7507.
14. (c) Chang, S.; Lee, M.; Ko, S.; Lee, P. H. Synth. Commun. 2002, 32, 1279.
15. (d) Lee, M.; Ko, S.; Chang, S. J. Am. Chem. Soc. 2000, 122, 12011.
16. (e) Chang, S.; Na, Y.; Choi, E.; Kim, S. Org. Lett. 2001, 3, 2089.
17. (f) Yang, S. H.; Chang, S. Org. Lett. 2001, 3, 4209.
18. (g) Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750.
19. For some recent examples, see: (a) Karlsson, U.; Wang, G.-Z.; Bäckvall, J.-E. J. Org. Chem. 1994, 59, 1196.
20. (b) Gendre, P. L.; Offenbecher, M.; Bruneau, C.; Dixneuf, P. H. Tetrahedron: Asymmetry 1998, 9, 2279.
21. (d) Lee, D.; Huh, E. A.; Kim, M-J.; Jung, H. M.; Koh, J. H.; Park, J. Org. Lett. 2000, 2, 2377.
22. (e) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801.
23. (f) Iwasa, S.; Takezawa, F.; Tuchiya, Y.; Nishiyama, H. Chem. Commun. 2001, 59.
24. 2/g, 1.25 g) in benzene (37 mL) was added the ruthenium complex 1 (250 mg), and the mixture was stirred for 14 h at room temperature. The mixture was filtered and washed with DMF, methanol, and hot benzene, and the filtered solid was dried under vacuum at 50-60 °C for 24 h.
25. 2, 1.2 wt % in 1,4-dioxane, and 2.1 wt % in THF).
26. 3/C was prepared and used for the oxidative cleavage of vicinal diols; see: Takezawa, E.; Sakaguchi, S.; Ishii, Y. Org. Lett. 1999, 1, 713.
27. 1H NMR of filtrate after the adsorption procedure.
28. It is based on the elemental analysis of the prepared solid-supported complex.
29. 3 was not replenished.
30. For references, see: (a) Arends, I. W. C. E.; Sheldon, R. A.; Wallau, M.; Schuchardt, U. Angew. Chem., Int. Ed. Engl. 1997, 36, 1144.
31. (b) Sheldon, R. A.; Wallau,; Arends, I. W. C. E.; Schuchardt, U. Acc. Chem. Res. 1998, 31, 485.