Metal-dependent halogenation and/or coupling reactions of porphyrins with PhIX2 (X = Cl, F)

Synlett

Volumn , Issue 19, 2005, Pages 2893-2898

  Jin, Li Mei ^a   Yin, Juan Juan ^b   Chen, Liang ^c   Guo, Chan Cheng ^c   Chen, Qing Yun ^a,c  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^c HUNAN UNIVERSITY   (China)

Author keywords

Chlorination; Coupling reaction; Iodination; Porphyrinoids; Synthetic methods

Indexed keywords

CHLORINE DERIVATIVE; COPPER DERIVATIVE; FLUORINE DERIVATIVE; IODINE DERIVATIVE; METAL DERIVATIVE; METALLOPORPHYRIN; NICKEL COMPLEX; PORPHYRIN DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHLORINATION; COMPLEX FORMATION; FLUORINATION; HALOGENATION; IODINATION; SUBSTITUTION REACTION;

EID: 28844472949     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918957     Document Type: Article

References (32)

1. (a) Burrell, A. K.; Officer, D. L.; Plieger, P. G.; Reid, D. C. W. Chem. Rev. 2001, 101, 2751.
2. (b) Wasielewski, M. R. Chem. Rev. 1992, 92, 435.
3. Holten, D.; Bocian, D. F.; Lindsey, J. S. Acc. Chem. Res. 2002, 35, 57.
4. (a) Aratani, N.; Osuka, A.; Kim, Y. H.; Jeong, D. H.; Kim, D. Angew. Chem. Int. Ed. 2000, 39, 1458.
5. (b) Piet, J. J.; Taylor, P. N.; Anderson, H. L.; Osuka, A.; Warman, J. M. J. Am. Chem. Soc. 2000, 122, 1749.
6. Ogawa, K.; Kobuke, Y. Angew. Chem. Int. Ed. 2000, 39, 4070.
7. Bonifazi, D.; Diederich, F. Chem. Commun. 2002, 2178.
8. (e) Aratani, N.; Cho, H. S.; Ahn, T. K.; Cho, S.; Kim, D.; Sumi, H.; Osuka, A. J. Am. Chem. Soc. 2003, 125, 9668.
9. Susumu, K.; Shimidzu, T.; Tanaka, K.; Segawa, H. Tetrahedron Lett. 1996, 37, 8399.
10. (a) Khoury, R. G.; Jaquinod, L.; Smith, K. M. Chem. Commun. 1997, 1057.
11. (b) Osuka, A.; Shimidzu, H. Angew. Chem. Int. Ed. 1997, 36, 135.
12. (c) Senge, M. O.; Feng, X. Tetrahedron Lett. 1999, 40, 4165.
13. (d) Shi, X.; Liebeskind, L. S. J. Org. Chem. 2000, 65, 1665.
14. Jin, L. M.; Chen, L.; Yin, J. J.; Guo, C. C.; Chen, Q. Y. Eur. J. Org. Chem. 2005, 3994.
15. Sawaguchi, M.; Ayuba, S.; Hara, S. Synthesis 2002, 1802.
16. Clausen, C.; Gryko, D. T.; Yasseri, A. A.; Diers, J. R.; Bocian, D. F.; Kuhr, W. G.; Lindsey, J. S. J. Org. Chem. 2000, 65, 7371.
17. +, 1211.3979; found, 1211.3981.
18. 2O: C, 71.58; H, 3.72; N, 8.48; Cl, 5.57. Found: C, 71.49; H, 3.76; N, 8.64; Cl, 5.87.
19. -1, crystal size 0.516 × 0.275 × 0.221 mm, R1 = 0.0981, wR2 = 0.2829, GOF = 0.963 [I > 2σ(I)]. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre (CCDC 281147). These data can be obtained free of charge at www.ccdc.cam.ac.uk/Data_request/cif or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44 (1223)336033; E-mail: deposit@ccdc.cam.ac.uk.
20. DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983.
21. +, 531.1138; found, 531.1136.
22. +, 923.3605; found, 923.3614.
23. (a) Adler, A. D.; Longo, F. R.; Finarelli, J. D.; Goldmacher, J.; Assour, J.; Korsakoff, L. J. Org. Chem. 1967, 32, 476.
24. (b) Bhyrappa, P.; Krishnan, V. Inorg. Chem. 1991, 30, 239.
25. +, 769.2576; found, 769.2585.
26. 6 as supporting electrolyte at r.t. [Glass-carbon working electrode, Pt disk (2 mm diameter) reference electrode, Pt wire counter electrode.]
27. (a) Carpenter, W. J. Org. Chem. 1966, 31, 2688.
28. (b) Arrica, M. A.; Wirth, T. Eur. J. Org. Chem. 2005, 395.
29. 2, 1102.1142; found, 1102.1187.
30. +, 733.10705; found, 733.1091.
31. Nakano, A.; Shimidzu, H.; Osuka, A. Tetrahedron Lett. 1998, 39, 9489.
32. Boyle, R. W.; Johnson, C. K.; Dolphin, D. J. Chem. Soc., Chem. Commun. 1995, 527.