Chemoselective hydrogenation of nitroarenes with carbon nanofiber-supported platinum and palladium nanopraticles

Organic Letters

Volumn 10, Issue 8, 2008, Pages 1601-1604

  Takasaki, Mikihiro ^a   Motoyama, Yukihiro ^a   Higashi, Kenji ^a   Yoon, Seong Ho ^a   Mochida, Isao ^a   Nagashima, Hideo ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; NANOMATERIAL; PALLADIUM; PLATINUM;

ARTICLE; CHEMISTRY;

CARBON; HYDROGEN; NANOSTRUCTURES; PALLADIUM; PLATINUM;

EID: 44449142058     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800277a     Document Type: Article

References (31)

1. Reviews:
2. (a) Tafesh, A. M.; Weiguny, J. Chem. Rev. 1996, 96, 2035.
3. (b) Downing, R. S.; Kunkeler, P. J.; van Bekkum, H. Catal. Today 1997, 37, 121.
4. (c) Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
5. (d) Adams, J. P. J. Chem. Soc. Perkin Trans. 1 2002, 2586.
6. (a) Rylander, P. In Catalytic Hydrogenation in Organic Synthesis; Academic Press: New York, 1979; p 112.
7. (b) Baumeister, P.; Studer, M.; Roessler, F. In Handbook of Heterogeneous Catalysis; Ertl, G., Knözinger, H., Weitkamp, J., Eds.; Wiley-VCH: Weinheim, 1997; pp 2186-2209.
8. (c) Blaser, H.-U.; Siegrist, U.; Steiner, H.; Studer, M. In Fine Chemicals through Heterogeneous Catalysis; Sheldon, R. A., van Bekkum, H., Eds.; Wiley-VCH: Weinheim, 2001; p 389.
9. Representative papers:
10. (a) Greenfield, H.; Dovell, F. S. J. Org. Chem. 1967, 32, 3670.
11. (b) Baumeister, P.; Blaser, H. U.; Siegrist, U.; Studer, M. Catal. Org. React. 1998, 75, 207.
12. (c) Wu, G.; Huang, M.; Richards, M.; Poirier, M.; Wen, X.; Draper, R. W. Synthesis 2003, 1657.
13. (d) Lee, H.-Y.; An, M. Bull. Kor. Chem. Soc. 2004, 25, 1717.
14. 2/Sm system:
15. 2:
16. (g) Ichikawa, S.; Tada, M.; Iwasawa, Y.; Ikariya, T. Chem. Commun. 2005, 924. Pt/C in ionic liquid:
17. 2- hydrosilanes:
18. 6/DBU under microwave irradiation:
19. 2:
20. (k) Corma, A.; Serna, P. Science 2006, 313, 332, and references cited therein.
21. Blaser, H.-U. Science 2006, 313, 312, and references cited therein.
22. (a) Feldheim, D. L.; Foss, C. A., Jr. Metal Nanoparticles: Synthesis, Characterization, and Application; Marcel Dekker: New York, 2002.
23. (b) Catalyst Supports and Supported Catalysts; Stiles, A. B., Ed.; Butter-worths: Boston, 1987.
24. (c) Handbook of Heterogeneous Catalysis; Ertl, G., Knözinger, H., Weitkamp, J., Eds.; VCH: Weinheim, 1997.
25. The CNFs are classified into three types: graphite layers are perpendicular (platelet: CNF-P), parallel (tubular: CNF-T), and stacked obliquely (herringbone: CNF-H). These three CNFs can be synthesized selectively in large scales; see:
26. (a) Rodriguez, N. M. J. Mater. Res. 1993, 8, 3233.
27. (b) Tanaka, A.; Yoon, S.-H.; Mochida, I. Carbon 2004, 42, 591; 1291.
28. (a) Motoyama, Y.; Takasaki, M.; Higashi, K.; Yoon, S.-H.; Mochida, I.; Nagashima, H. Chem. Lett. 2006, 35, 876.
29. (b) Takasaki, M.; Motoyama, Y.; Higashi, K.; Yoon, S.-H.; Mochida, I.; Nagashima, H. Chem. Asian J. 2007, 2, 1524.
30. (c) Takasaki, M.; Motoyama, Y.; Yoon, S.-H.; Mochida, I.; Nagashima, H. J. Org. Chem. 2007, 72, 10291.
31. No reduction took place in the reaction of aliphatic nitro compounds.