Practical and efficient synthesis of various meso-functionalized porphyrins via simple ligand-free nickel-catalyzed C-O, C-N, and C-C cross-coupling reactions

Journal of Organic Chemistry

Volumn 72, Issue 8, 2007, Pages 2732-2736

  Liu, Chao ^a   Shen, Dong Mei ^a   Chen, Qing Yun ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE COMPOUNDS; CATALYSIS; LIGANDS; NICKEL; NUCLEOPHILES; PORPHYRINS;

CENTRAL METAL IONS; CROSS-COUPLING; MESO-BROMOPORPHYRINS;

SYNTHESIS (CHEMICAL);

CARBON; LIGAND; NICKEL; NITROGEN; OXYGEN; PORPHYRIN DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; SYNTHESIS;

EID: 34247338978     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0618728     Document Type: Article

References (31)

1. The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000-2003; Vols. 1-20.
2. For selective and recent reviews on transition-metal-catalyzed cross-coupling reactions, see: (a) de Meijere, A., Diederich, F., Eds. Metal-Catalyzed Cross-Coupling Reactions; Wiley: Weinheim, 2004.
3. (b) Montgomery, T. Angew. Chem., Int. Ed. 2004, 43, 3890-3908.
4. (c) Li, Z.; Fu, Y.; Liu, L.; Guo, Q.-X. Chin. J. Org. Chem. 2005, 25, 1508-1529.
5. (d) Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041-2075.
6. For recent and selective reports on porphyrin functionalization by transition-metal-catalyzed cross-coupling reactions of bromoporphyrins, see: (a) Shen, D. M.; Liu, C.; Chen, Q. Y. J. Org. Chem. 2006, 71, 6508.
7. (b) Liu, C.; Shen, D. M.; Chen, Q. Y. Eur. J. Org. Chem. 2006, 2703.
8. (c) Liu, C.; Chen, Q. Y. Synlett 2005, 8, 1306.
9. (d) Liu, C.; Chen, Q. Y. Eur. J. Org. Chem. 2005, 3680.
10. (e) Gao, G. Y.; Colvin, A. J.; Chen, Y.; Zhang, X. P. J. Org. Chem. 2004, 69, 8886.
11. (f) Gao, G. Y.; Chen, Y.; Zhang, X. P. Org. Lett. 2004, 6, 1837.
12. (g) Gao, G. Y.; Colvin, A. J.; Chen, Y.; Zhang, X. P. Org. Lett. 2003, 5, 3261.
13. (h) Gao, G. Y.; Chen, Y.; Zhang, X. P. J. Org. Chem. 2003, 68, 6215.
14. (i) Chen, Y.; Zhang, X. P. J. Org. Chem. 2003, 68, 4432.
15. (J) Takanami, T.; Hayashi, M.; Hino, F.; Suda, K. Tetrahedron Lett. 2003, 44, 7353.
16. (k) Khan, M. M.; Ali, H.; Van Lier, J. E. Tetrahedron Lett. 2001, 42, 1615.
17. (l) Cheng, L. L.; Chang, C. J.; Nocera, D. G. J. Org. Chem. 2003, 68, 4075.
18. (m) Vas, B.; Alvarez, R.; Nieto, M.; Paniello, A. I.; de Lera, A. R. Tetrahedron Lett. 2001, 42, 7409.
19. (n) Deng, Y.; Chang, C. K.; Nocera, D. G. Angew. Chem., Int. Ed. 2000, 39, 1066.
20. (o) Iovine, P. M.; Kellett, M. A.; Redmore, N. P.; Therien, M. J. J. Am. Chem. Soc. 2000, 122, 8717.
21. (p) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228.
22. (q) Shi, X.; Amin, R.; Liebeskind, L. S. J. Org. Chem. 2000, 65, 1650.
23. (r) Sharman, W. M.; Van Lier, J. E. J. Porphyrins Phthalocyanines 2000, 4, 441 and references cited therein.
24. (a) Liu, C.; Shen, D. M.; Chen, Q. Y. Chem. Commun. 2006, 770.
25. (b) Shen, D. M.; Liu, C.; Chen, Q. Y. Chem. Commun. 2005, 4982.
26. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
27. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
28. (c) Miyaura, N. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, p 11.
29. (d) Kotha, S.; Lahiri, K. Kashinath, D. Tetrahedron 2002, 58, 9633.
30. (e) Bellina. F.; Carpita, A.; Rossi, R. Synthesis 2004, 2419.
31. (f) Felpin, F.-X.; Ayad, T.; Mitra, S. Eur. J. Org. Chem. 2006, 2679.