General and efficient synthesis of meso- and β-perfluoroalkylated porphyrins via Pd-catalyzed cross-coupling reaction

Synlett

Volumn , Issue 8, 2005, Pages 1306-1310

  Liu, Chao ^a   Chen, Qing Yun ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

AsPh3; Brominated porphyrins; Pd 2(dba)3 CHCl3; Perfluoroalkylation

Indexed keywords

ALKYL GROUP; COPPER; IODIDE; METAL ION; NICKEL; PALLADIUM; PERFLUORO COMPOUND; PORPHYRIN DERIVATIVE; TETRAPHENYLPORPHYRIN DERIVATIVE; ZINC;

ALKYLATION; ARTICLE; BROMINATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CYCLIZATION; FLUORINATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 19844381828     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-868484     Document Type: Article

References (38)

1. The Porphyrin Handbook, Vol 1-20; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: San Diego, 2000-2003.
2. (a) Binbaum, E. R.; Schaefer, W. P.; Labingev, J. A.; Bercaw, J. E.; Gray, H. B. Inorg. Chem. 1995, 34, 1751.
3. (b) Campestrini, S.; Lora, G.; Tonellato, U. Tetrahedron Lett. 2001, 42, 7045.
4. (c) Woller, E. K.; DiMagno, S. G. J. Org. Chem. 1997, 62, 1588.
5. (d) DiMagno, S. G.; Wertsching, A. K.; Rossa, G. R. J. Am. Chem. Soc. 1995, 117, 8279.
6. (e) Takeuchi, T.; Gray, H. B.; Godciardi, W. A. J. Am. Chem. Soc. 1994, 116, 9730.
7. (f) Moore, K. T.; Fletcher, J. T.; Therin, M. J. J. Am. Chem. Soc. 1999, 121, 5196.
8. (g) Taniguchi, M.; Ra, D.; Mo, G.; Balasubramanian, T.; Lindsey, J. S. J. Org. Chem. 2001, 66, 7342.
9. (h) Pozzi, G.; Montanari, F.; Quici, S. Chem. Commun. 1997, 69.
10. (i) Barkigia, K. M.; Battioni. P.; Riou, V.; Mansuy, D.; Fajev, J. Chem. Commun. 2002, 956.
11. DiMagno, S. G.; Dussacet, P. H.; Schulty, J. A. J. Am. Chem. Soc. 1996, 118, 5312.
12. (a) Zeng, Z.; Liu, C.; Jin, L. M.; Guo, C. C.; Chen, Q. Y. Eur. J. Org. Chem. 2005, 306.
13. (b) Jin, L. M.; Zeng, Z.; Guo, C. C.; Chen, Q. Y. J. Org. Chem. 2003, 68, 3912.
14. (c) Wijesekera, T. P. Can. J. Chem. 1996, 74, 1868.
15. (d) Goll, J. G.; Moore, K. T.; Ghosh, A.; Therien, M. J. J. Am. Chem. Soc. 1996, 118, 8344.
16. (e) DiMagno, S. G.; Williams, R. A.; Therine, M. J. J. Org. Chem. 1994, 59, 6943.
17. (f) Michihide, H.; Katsuhiro, A.; Yasuhiro, A.; Hisanobu, O. Tetrahedron Lett. 1983, 24, 4343.
18. (g) Ralph, W. K.; LeGoff, E. J. Org. Chem. 1982, 47, 5243.
19. For recent and selective reports on the transition metal-catalyzed cross-coupling reactions for porphyrin synthesis, see: (a) Gao, G. Y.; Colvin, A. J.; Chen, Y.; Zhang, X. P. J. Org. Chem. 2004, 69, 8886.
20. (b) Gao, G. Y.; Chen, Y.; Zhang, X. P. Org. Lett. 2004, 6, 1837.
21. (c) Gao, G. Y.; Colvin, A. J.; Chen, Y.; Zhang, X. P. Org. Lett. 2003, 5, 3261.
22. (d) Gao, G. Y.; Chen, Y.; Zhang, X. P. J. Org. Chem. 2003, 68, 6215.
23. (e) Chen, Y.; Zhang, X. P. J. Org. Chem. 2003, 68, 4432.
24. (f) Takanami, T.; Hayashi, M.; Hino, F.; Suda, K. Tetrahedron Lett. 2003, 44, 7353.
25. (g) Khan, M. M.; Ali, H.; Van Lier, J. E. Tetrahedron Lett. 2001, 42, 1615.
26. (h) Cheng, L. L.; Chang, C. J.; Nocera, D. G. J. Org. Chem. 2003, 68, 4075.
27. (i) Vas, B.; Alvarez, R.; Nieto, M.; Paniello, A. I.; de Lera, A. R. Tetrahedron Lett. 2001, 42, 7409.
28. (j) Deng, Y.; Chang, C. K.; Nocera, D. G. Angew. Chem. Int. Ed. 2000, 39, 1066.
29. (k) Iovine, P. M.; Kellett, M. A.; Redmore, N. P.; Therien, M. J. J. Am. Chem. Soc. 2000, 122, 8717.
30. (l) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228.
31. (m) Shi, X.; Amin, R.; Liebeskind, L. S. J. Org. Chem. 2000, 65, 1650.
32. (n) Sharman, W. M.; Van Lier, J. E. J. Porphyrins Phthalocyanines 2000, 4, 441; and references cited therein.
33. (a) Arnold, D. P.; Bott, R. C.; Eldridge, H.; Elms, F. M.; Smith, G.; Zojaji, M. Aust. J. Chem. 1997, 50, 495.
34. (b) DiMagno, S. G.; Lin, V. S. Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983.
35. Callot, H. J. Bull. Soc. Chim. Fr. 1974, 1492.
36. Kumar, D. K.; Bhyrappa, P.; Varghese,B. Tetrahedron Lett. 2003, 40, 4849.
37. Bhyrappa, P.; Krishnan, V. Inorg. Chem. 1991, 30, 239.
38. McLoughlin, V. C. R.; Thrower, J. Tetrahedron 1969, 25, 5921.