One-pot synthesis of substituted 2,2'-bipyrroles. A straightforward route to aryl porphycenes

Organic Letters

Volumn 11, Issue 1, 2009, Pages 77-79

  Sánchez García, David ^a   Borrell, José I ^a   Nonell, Santi ^a  

^a INSTITUT QUÍMIC DE SARRIÀ   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYCENE; PORPHYRIN; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PORPHYRINS; PYRROLES; STEREOISOMERISM;

EID: 59649094199     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802380g     Document Type: Article

References (26)

1. Rapoport, H.; Castagnoli, N. J. Am. Chem. Soc. 1962, 84, 2178-2181.
2. Rapoport, H.; Holden, K. G. J. Am. Chem. Soc. 1962, 84, 635-642.
3. Bonnett, R.; Cannon, J. R.; Clark, V. M.; Johnson, A. W.; Parker, L. F. J.; Smith, E. L.; Todd, A. J. Chem. Soc. 1957, 1158.
4. Benincori, T.; Brenna, E.; Sannicolò, F.; Zotti, G.; Zecchin, S.; Schiavon, G.; Gatti, C.; Frigerio, G. Chem. Mater. 2000, 12, 1480-1489.
5. Sessler, J. L.; Weghorn, S. J. Expanded, Contracted, and Isomeric Porphyrins; Elsevier: Oxford, 1997.
6. Vogel, E.; Kocher, M.; Schmickler, H.; Lex, J. Angew. Chem. Int. Ed. Engl. 1986, 25, 257-259.
7. Bauer, V. J.; Clive, D. R.; Dolphin, D.; Paine, J. B.; Harris, F. L.; King, M. M.; Loder, J.; Wang, S.-W. C.; Woodward, R. B. J. Am. Chem. Soc. 1983, 105, 6429-6436.
8. Seidel, D.; Lynch, V.; Sessler, J. L. Angew. Chem., Int. Ed. 2002, 41, 1422-1425.
9. Stepien, M.; Donnio, B.; Sessler, J. L. Angew. Chem. Int. Ed. 2007, 46, 1431-1435.
10. Stockert, J. C.; Cañete, M.; Juarranz, A.; Villanueva, A.; Horobin, R. W.; Borrell, J. I.; Teixidó, J.; Nonell, S. Curr. Med. Chem. 2007, 14, 997-1026.
11. Merrill, B. A.; LeGoff, E. J. J. Org. Chem. 1990, 55, 2904-2908.
12. (a) Grigg, R.; Johnson, A. W.; Wasley, J. W. F. J. Chem. Soc. 1963, 359-366.
13. (b) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80-87.
14. (c) Groenendaal, L.; Peerlings, H. W. I.; Havinga, E. E.; Vekemans, J. A. J. M.; Meijer, E. W. Synth. Met. 1995, 69, 467-470.
15. Arad, O.; Morros, J.; Batllori, X.; Teixidó, J.; Nonell, S.; Borrell, J. I. Org. Lett. 2006, 8, 847-850.
16. (a) Falk, H.; Flodl, H. Monatsh. Chem. 1988, 119, 247-252.
17. (b) Sessler, J. L.; Aguilar, A.; Sánchez-García, D.; Seidel, D.; Köhler, Th.; Arp, F.; Lynch, V. M. Org. Lett. 2005, 7, 1887-1890.
18. Boger, D. L.; Patel, M. J. Org. Chem. 1988, 53, 1405-1415.
19. Gribble, G W.; Blank, D. H.; Jasinski, J. P. Chem. Commun. 1999, 2195-2196.
20. Dohi, T.; Morimoto, K.; Ito, M.; Kita, Y. Synthesis 2007, 18, 2913-2919.
21. Urbanska, N.; Pietraszkiewicz, M.; Waluk, J. J. Porphyrins Phthalocyanines 2007, 11, 596-600.
22. Dijkstra, H. P.; ten Have, R.; van Leusen, A. M. J. Org. Chem. 1998, 63, 5332-5338.
23. Beddoes, R. L.; Cheeseright, T.; Wang, J.; Quayle, P. Tetrahedron Lett. 1995, 36, 283-286.
24. Sánchez-García, D.; Sessler, J. L. Chem. Soc. Rev. 2008, 37, 215-232.
25. Jiao, L.; Hao, E.; Vicente, M. G. H.; Smith, K. M. J. Org. Chem. 2007, 72, 8119-8122.
26. Nonell, S.; Bou, N.; Borrell, J. I.; Teixidó, J.; Villanueva, A.; Juarranz, A.; Cañete, M. Tetrahedroron Lett. 1995, 36, 3405-3408.