Reusable Cu2O/PPh3/TBAB system for the cross-couplings of aryl halides and heteroaryl halides with terminal alkynes

Journal of Organic Chemistry

Volumn 72, Issue 16, 2007, Pages 6294-6297

  Tang, Bo Xiao ^a   Wang, Feng ^a   Li, Jin Heng ^a   Xie, Ye Xiang ^a   Zhang, Man Bo ^a  

^a HUNAN NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CATALYSTS; COPPER; NANOPARTICLES;

ALKYNES; ALKYNOLS; ARYL HALIDES; CROSS-COUPLINGS; HETEROARYL HALIDES;

HALOGEN COMPOUNDS;

ALKYNE DERIVATIVE; COPPER DERIVATIVE; HALIDE; NANOPARTICLE; ALKYNE; CARBON; CARBON NANOTUBE; COPPER; HALOGEN; PHOSPHINE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYST; CROSS COUPLING REACTION; RECYCLING; SONOGASHIRA REACTION; TEMPERATURE; CHEMICAL MODEL; CHEMISTRY; INSTRUMENTATION; METHODOLOGY; NANOTECHNOLOGY; ORGANIC CHEMISTRY;

ALKYNES; CARBON; CHEMISTRY, ORGANIC; COPPER; HALOGENS; MODELS, CHEMICAL; NANOTECHNOLOGY; NANOTUBES, CARBON; PHOSPHINES;

EID: 34547613945     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070538o     Document Type: Article

References (30)

1. For special reviews on copper-catalyzed cross-couplings, see: (a) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int Ed. 2000, 39, 2632.
2. (b) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
3. (c) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
4. (d) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
5. For papers on the Sonogashira cross-coupling reaction catalyzed by a catalytic amount of copper, see: (a) Okuro, K.; Furuune, M.; Enna, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 4716.
6. (b) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315.
7. (c) Ma, D, Liu, F. Chem. Commun. 2004, 1934.
8. (d) Wang, Y. F.; Deng, W.; Liu, L.; Guo, Q. X. Chin. Chem. Lett. 2005, 16, 1197.
9. (e) Saejueng, P.; Bates, C. G.; Venkataraman, D. Synthesis 2005, 1706.
10. (f) Xie, Y.-X.; Deng, C.-L.; Pi, S.-F.; Li, J.-H.; Yin, D.-L. Chin. J. Chem. 2006, 24, 1290.
11. (g) Guo, S.-M.; Deng, C.-L.; Li, J.-H. Chin. Chem. Lett. 2007, 18, 13.
12. (h) Li, J.-H.; Li, J.-L.; Wang, D.-P.; Pi, S.-F.; Xie, Y.-X.; Zhang, M.-B.; Hu, X.-C. J. Org. Chem. 2007, 72, 2053.
13. (i) Thathagar, M. B.; Beckers, J.; Rothenberg, G. Green Chem. 2004, 6, 215.
14. (j) Li, J.-H.; Li, J.-L.; Xie, Y.-X. Synthesis 2007, 984.
15. For reviews, see: (a) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, Germany, 1998.
16. (b) Miyaura, N. Cross-Coupling Reaction; Springer: Berlin, 2002.
17. (c) de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions: Wiley-VCH: Weinheim, Germany, 2004.
18. (d) Doucei, H.; Hierso, J.-C. Angew. Chem., Int. Ed. 2007, 46, 834.
19. (e) Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874.
20. 2O nanoparticles, see: (a) Xu, H.; Wang, W.; Zhu, W. J. Phys. Chem. B 2006, 110, 13829.
21. (b) Ng, C. H. B.; Fan, W. Y. J. Phys. Chem. B 2006, 110, 20801.
22. 2O nanoparticles, see: (a) Guo, L.; Murphy, C. J. Nano Lett. 2003, 3, 231.
23. (b) Zeng, X.-W.; Zhang, Y.-H.; Luo, C.-C.; Zeng, Y.-W.; Wang, Y.-G. Chin. J. Inorg. Chem. 2005, 21, 1515.
24. (c) Singh, D. P.; Neti, N. R.; Sinha, A. S. K.; Srivastava, O. N. J. Phys. Chem. C 2007, 111, 1584.
25. 2O nanoparticles, see: (a) Cao, M.; Hu, C.; Wang, Y.; Guo, Y.; Guo, C.; Wang, E. Chem. Commun. 2003, 1884.
26. (b) Zhang, J.; Liu, J.; Peng, Q.; Wang, X.; Li, Y. Chem. Mater. 2006, 18, 867.
27. (c) Wu, W.-T.; Wang, Y.; Shi, L.; Pang, W.; Zhu, Q.; Xu, G.; Lu, F. J. Phys. Chem. B 2006, 110, 14702.
28. (d) Yao, W.-T.; Yu, S.-H.; Zhou, Y.; Jiang, J.; Wu, Q.-S.; Zhang, L.; Jiang, J. J. Phys. Chem. B 2005, 109, 14011.
29. For selected papers, see: (a) Li, J.-H.; Tang, B.-X.; Tao, L.-M.; Liang, Y.; Zhang, M.-B. J. Org. Chem. 2006, 71, 7488.
30. (b) White, B.; Yin, M.; Hall, A.; Sergey, D. L.; Rahman, T.; Turro, N.; O'Brien, S. Nano Lett. 2006, 6, 2095.