Efficient microwave-assisted synthesis of amine-substituted tetrakis(pentafluorophenyl)porphyrin

Organic Letters

Volumn 8, Issue 22, 2006, Pages 4985-4988

  Samaroo, Diana ^a   Soll, Clifford E ^a   Todaro, Louis J ^a   Drain, Charles M ^a,b  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b ROCKEFELLER UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; PORPHYRIN;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; MICROWAVE RADIATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMINES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; MICROWAVES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PORPHYRINS; STEREOISOMERISM;

EID: 33750921786     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060946z     Document Type: Article

References (20)

1. (a) Benaglia, M.; Danelli, T.; Fabris, F.; Sperandio, D.; Pozzi, G. Org. Lett. 2002, 4, 4229.
2. (b) Yang, J.; Weinberg, R.; Breslow, R. Chem. Commun. 2000, 531.
3. Drain, C. M.; Hupp, J. T.; Suslick, K. S.; Wasielewski, M. R.; Chen, X. J. Porphyrins Phthalocyanines 2002, 6, 243.
4. (a) Chen, X.; Hui, L.; Foster, D. A.; Drain, C. M. Biochemistry 2004, 43, 10918.
5. (b) Sylvain, I.; Zerrouki, R.; Granet, R.; Huang, Y. M.; Lagorce, J.-F.; Guilloton, M.; Blais, J.-C.; Krausz, P. Bioorg. Med. Chem. 2002, 10, 57.
6. (c) Pasetto, P.; Chen, X.; Drain, C. M.; Franck, R. W. Chem. Commun. 2001, 82.
7. Sauer, D. R.; Kalvin, D.; Phelan, K. M. Org. Lett. 2003, 5, 4721.
8. Yoon, D. S.; Han, Y.; Stark, T. M.; Haber, J. C.; Gregg, B. T.; Stankovich, S. B. Org. Lett. 2004, 6, 4775.
9. (a) Liu, M. O.; Tai, C.-H.; Wang, W.-Y.; Chen, J.-R.; Hu, A. T.; Wei, T.-H. J. Organomet. Chem. 2004, 689, 1078.
10. (b) Liu, M. O.; Hu, A. T. J. Organomet. Chem. 2004, 689, 2450.
11. (c) Boufatah, N.; Gellis, A.; Maldonado, J.; Vanelle, P. Tetrahedon 2004, 60, 9131.
12. ) Drain, C. M.; Gong, X. Chem. Commun. 1997, 2117.
13. ) (a) Chaouchi, M.; Loupy, A.; Marque, S.; Petit, A. Eur. J. Org. Chem. 2002, 1278.
14. (b) Mojtahedi, M. M.; Saidi, M. R.; Shirzi, J. S.; Bolourtchian, M. Synth. Commun. 2002, 32, 851.
15. (a) Shaw, S. J.; Elgie, K. J.; Edwards, C.; Boyle, R. W. Tetrahedron Lett. 1999, 40, 1595.
16. (b) Suzuki, M.; Shimizu, S.; Shin, J.-Y.; Osuka, A. Tetrahedron Lett. 2003, 44, 4597.
17. (c) Battioni, P.; Brigaud, O.; Desvaux, H.; Mansuy, D.; Traylor, T. G. Tetrahedron Lett. 1991, 32, 2893.
18. (a) Molineux, G. Pharmacotherapy 2003, 23, 3S.
19. (b) Hamblin, M. R.; Miller, J. L.; Rizvi, I.; Ortel, B.; Maytin, E. V.; Hasan, T. Cancer Res. 2001, 61, 7155.
20. tboc EDA (Quanta BioDesign) in NMP (0.1 mL). The closed vial was irradiated using a domestic microwave oven (1100 W, Samsung MW4250W) at 2 min intervals until no starting material was visualized by TLC (10 min). After the vial was cooled, the solvent (NMP) was removed in vacuo. The reaction mixture was purified on a silica gel prep TLC plate (hexane/ethyl acetate/methanol, 2:1.5:0.5). The porphyrin was redissolved in methanol and evaporated under reduced pressure to afford >90% yield.