Pd-catalyzed dehalogenation of aromatic halides under solvent-free conditions using hydrogen balloon

Bulletin of the Korean Chemical Society

Volumn 32, Issue 3, 2011, Pages 1074-1076

  Chang, Fei ^a   Kim, Hakwon ^b   Lee, Byeongno ^b   Park, Hoon Gyu ^b   Park, Jaiwook ^c  

^a UNIVERSITY OF SHANGHAI FOR SCIENCE AND TECHNOLOGY   (China)

^b Kyung Hee University   (South Korea)

^c Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

Aluminum oxyhydroxide; Aromatic halides; Dehalogenation; Pd nanoparticles; Solvent free reaction

Indexed keywords

EID: 79953242505     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2011.32.3.1074     Document Type: Article

References (28)

1. Alonso, F.; Beletskava, I. P.; Yus, M. Chem. Rev. 2002, 102, 4009.
2. Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047.
3. Martins, M. A. P.; Frizzo, C. P.; Moreira, D. N.; Buriol, L.; Machado, P. Chem. Rev. 2009, 109, 4140.
4. Tanaka, K; Toda, F. Chem. Rev. 2000, 100, 1025.
5. Haggblom, M. M.; Ahn, Y. B.; Fennell, D. E.; Kerkhof, L. J.; Rhee, S. K. Adv. Appl. Microbiol. 2003, 53, 61.
6. Zinovyev, S.; Shelepchikov, A.; Tundo, P. Appl. Catal. B 2007, 72, 289.
7. Keane, M. A.; Pina, G.; Tavoularis, G. Appl. Catal. B 2004, 48, 275.
8. Iranpoor, N.; Firouzabadi, H.; Azadi, R. J. Organomet. Chem. 2010, 695, 887.
9. Navarro, O.; Marion, N.; Oonishi, Y.; Kelly, R. A.; Nolan, S. P. J. Org. Chem. 2006, 71, 685.
10. Léger, B.; Nowicki, A.; Roucoux, A.; Rolland, J. P. J. Mol. Catal. A 2007, 266, 221.
11. Fujita, K.; Owaki, M.; Yamaguchi, R. Chem. Commun. 2002, 2964.
12. Mao, J.; Yan, X.; Gu, H.; Jiang, L. Chin. J. Catal. 2009, 30, 182.
13. Xu, Y.; Zhu, Y.; Zhao, F.; Ma, C. Appl. Catal. A 2007, 324, 83.
14. Monguchi, Y.; Kume, A.; Hattori, K.; Maegawa, T.; Sajiki, H. Tetrahedron 2006, 62, 7926.
15. Cellier, P. P.; Spindler, J. F.; Taillefer, M.; Cristau, H. J. Tetrahedron Lett. 2003, 44, 7191.
16. Howe, R. F. Appl. Catal. A 2004, 271, 3.
17. Kwon, M. S.; Kim, N.; Park, C. M.; Lee, J. S.; Kang, K. Y.; Park, J. Org. Lett. 2005, 7, 1077.
18. Kwon, M. S.; Kim, N.; Seo, S. H.; Park, I. S.; Cheedrala, R. K.; Park, J. Angew. Chem. Int. Ed. 2005, 44, 6913.
19. Kwon, M.; Kim, S.; Park, S.; Bosco, W.; Chidrala, R. K.; Park, J. J. Org. Chem. 2009, 74, 2877.
20. Chang, F.; Kim, H.; Lee, B.; Park, S.; Park, J. Tetrahedron Lett. 2010, 51, 4250.
21. Wang, J.; Zhu, Z.; Huang, W.; Deng, M.; Zhou, X. J. Organomet. Chem. 2008, 693, 2188.
22. Pri-Bar, I.; James, B. R. J. Mol. Catal. A 2007, 264, 135.
23. Hara, T.; Mori, K., Oshiba, M.; Mizugaki, T., Ebitani, K.; Kaneda, K. Green Chem. 2004, 6, 507.
24. 16a GC analysis was performed on an ACME 6000 GC equipped with THERMO TR-WaxMS column (30 m × 0.25 mm ID × 0.25 μm) and FID detector. Typical procedure of solvent-free dehalogenation of 4-chlorophenol is described as follows: the mixture of solid 4-chlorophenol (0.2 mmol) and Pd/ AlO(OH) (2.0 mol % of Pd) was ground finely with a mortar and pestle at ambient temperature before use, and then put into a glassware equipped with a rubber septa, followed by sealing with parafilm. Nitrogen gas was charged into the reactor for several times to expel air and then expelled by atmospheric pressure of hydrogen. The mixture was allowed to react for a desired time without controlling the temperature in the vessel. After filtering the catalyst, the product analyses were performed using GC and 1H NMR by comparing to the authentic samples. Dehalogenation in organic solvents: the mixture of 4-chlorophenol and Pd/ AlO(OH) (2.0 mol % of Pd) in organic solvent (3 mL) was exposed to atmospheric hydrogen environment at room temperature. After reaction, the analysis procedure was the same as described above.
25. Studer, M.; Blaser, H. U. J. Mol. Catal. A 1996, 112, 437.
26. Aramendia, M. A.; Borau, V.; Garcia, I. M.; Jimenez, C.; Lafont, F.; Marinas, A.; Marinas, J. M.; Urbano, F. J. J. Mol. Catal. A 2002, 184, 237.
27. Levine, M.; Temin, S. C. J. Org. Chem. 1957, 22, 85.
28. Koo, J. J. Am. Chem. Soc. 1953, 75, 720.