CO2 as both a selective agent and reaction media in palladium-catalyzed reductive Ullmann-type coupling reaction

Chinese Journal of Chemistry

Volumn 22, Issue 9 SPEC.ISS., 2004, Pages 966-970

  Li, Jin Heng ^a   Xie, Ye Xiang ^a  

^a HUNAN NORMAL UNIVERSITY   (China)

Author keywords

A selective agent; Aryl halide; Carbon dioxide; Palladium; Reaction media; Ullmann type coupling reaction

Indexed keywords

CARBON DIOXIDE; CHLORIDE; HALIDE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; ROOM TEMPERATURE; SYNTHESIS;

EID: 7044233385     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.20040220918     Document Type: Article

References (37)

1. (a) Jia, L.-Q.; Jiang, H.-F.; Li, J.-H. Chem. Commun. 1999, 985.
2. (b) Li, J.-H.; Jiang, H.-F. Chem. Commun. 1999, 2369.
3. (c) Li, J.-H.; Jiang, H.-F.; Chen, M.-C. Green Chem. 2001, 3, 137.
4. (d) Li, J.-H.; Jiang, H.-F.; Chen, M.-C. Chin. J. Chem. 2001, 19, 1153.
5. (e) Li, J.-H.; Xie, Y.-X.; Yin, D.-L.; Jiang, H.-F. Green Chem. 2002, 4, 424.
6. (f) Li, J.-H.; Xie, Y.-X.; Yin, D.-L.; Jiang, H.-F. Chin. J. Chem. 2003, 21, 714 and references cited therein.
7. (g) Brown, R. A.; Pollet, P.; Mckoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254.
8. For representative reviews, see: (a) Jessop, P. G. and Leitner, W., Chemical Synthesis Using Supercritical Fluids, Wiley-VCH, Weinheim, 1999.
9. (b) Jessop, P. G.; Ikariya, T.; Noyori, R. Chem. Rev. 1999, 99, 475.
10. (c) Li, J.; Jia, L.; Jiang, H. Chin. J. Org. Chem. 2000, 20, 293 (in Chinese).
11. (d) Oakes, R. S.; Clifford, A. A.; Rayner, C. M. J. Chem. Soc., Perkin Trans. 1 2001, 917.
12. (a) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977.
13. (b) Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312 and references cited therein.
14. For Ni catalyzed Ullmann-type couplings, see: (a) Takagi, K.; Hayama, N.; Sasaki, K. Bull. Chem. Soc. Jpn. 1984, 57, 1887.
15. (b) Meyer, G.; Rollin, Y.; Perichon, J. J. Organomet. Chem. 1987, 333, 263.
16. For Pd/C catalyzed Ullmann-type couplings using Zn and water as the reducing reagent, see: (a) Ventrakaman, S.; Li, C. J. Org. Lett. 1999, 1133.
17. (b) Ventrakaman, S.; Li, C. Tetrahedron Lett. 2000, 41, 4831 and references cited therein.
18. (c) Mukhopadhyay, S.; Rothenberg, G.; Gitis, D.; Sasson, Y. Org. Lett. 2000, 211.
19. (d) Li, J.-H.; Xie, Y.-X.; Yin, D.-L. J. Org. Chem. 2003, 68, 9867.
20. For Pd/C catalyzed Ullmann-type couplings using other reducing reagents, see: (I) Formate salts as the reducing reagent: (a) Mukhopadhyay, S.; Rothenberg, G.; Gitis, D.; Wiener, H.; Sasson, Y. J. Chem. Soc., Perkin Trans. 2 1999, 2481.
21. (b) Mukhopadhyay, S.; Rothenberg, G.; Qafisheh, N.; Sasson, Y. Tetrahedron Lett. 2001, 42, 6117.
22. (II) Hydrogen gas as the reducing reagent: (c) Mukhopadhyay, S.; Rothenberg, G.; Wiener, H.; Sasson, Y. Tetrahedron 1999, 55, 14763 and references cited therein.
23. For other Pd-catalyzed reductive Ullmann-type couplings, see: (a) Kuroboshi, M.; Waki, Y.; Tanaka, H. J. Org. Chem. 2003, 68, 3938 and references cited therein.
24. (b) Hassan, J.; Hathroubi, C.; Gozzi, C.; Lamaire, M. Tetrahedron 2001, 57, 7845.
25. (c) Hassan, J.; Penalva, V.; Lavenot, L.; Gozzi, C.; Lemaire, M. Tetrahedron 1998, 54, 13793.
26. (d) Penalva, V.; Hassan, J.; Lavenot, L.; Gozzi, C.; Lemaire, M. Tetrahedron Lett. 1998, 39, 2559.
27. (e) Hennings, D. D.; Iwama, T.; Rawel, V. H. Org. Lett. 1999, 1, 1205.
28. (a) Bamfield, P.; Quan, P. M. Synthesis 1978, 537.
29. (b) Hassan, J.; Penalva, V.; Lavenot, L.; Gozzi, C.; Lemaire, M. Tetrahedron 1998, 54, 13793.
30. (a) Peyrot F.; Martin, M.-T.; Migault, J.; Ducrocq, C. Eur. J. Org. Chem. 2003, 172.
31. (b) Li, J.-H; Xie, Y.-X.; Yin, D.-L. Green Chem. 2002, 4, 505.
32. (c) Gabriele, B.; Salerno, G.; Costa, M.; Chiusoli, G. P. Chem. Commun. 1999, 1381 and references cited therein.
33. Penso, M.; Albanese, D.; Landini, D.; Lupi, V. J. Mol. Catal. A: Chem. 2003, 204-205, 177.
34. Tamura, Y.; Chun, M. W.; Inoue, K.; Minamikawa, J. Synthesis 1978, 822.
35. Morkovnik, A. S. Zhur. Obsh. Khim. 1989, 59, 921.
36. Nassimbeni, L. R. J. Chem. Soc., Perkin Trans. 2 2002, 1246.
37. Goeran, L. J. Org. Chem. 1987, 52, 547.