Conversion of 4,4-difluoro-4-bora-3a, 4a-diaza-s-indacenes (F-BODIPYs) to dipyrrins with a microwave-promoted deprotection strategy

Organic Letters

Volumn 12, Issue 7, 2010, Pages 1424-1427

  Crawford, Sarah M ^a   Thompson, Alison ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

4,4 DIFLUORO 4 BORA 3A,4A DIAZA S INDACENE; 4,4-DIFLUORO-4-BORA-3A,4A-DIAZA-S-INDACENE; BORON DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MICROWAVE RADIATION; STEREOISOMERISM; SYNTHESIS;

BORON COMPOUNDS; MICROWAVES; MOLECULAR STRUCTURE; PYRROLES; STEREOISOMERISM;

EID: 77950228099     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol902908j     Document Type: Article

References (26)

1. Benniston, A. C.; Copley, G. Phys. Chem. Chem. Phys. 2009 11, 4124-4131.
2. Loudet, A.; Burgess, K. Chem. Rev. 2007 107, 4891-4932.
3. Ulrich, G.; Ziessel, R.; Harriman, A. Angew. Chem., Int. Ed. 2008 47, 1184-1201.
4. Ziessel, R.; Ulrich, G.; Harriman, A. New J. Chem. 2007 31, 496-501.
5. Goze, C.; Ulrich, G.; Mallon, L. J.; Allen, B. D.; Harriman, A.; Ziessel, R. J. Am. Chem. Soc. 2006 128, 10231-10239.
6. Goze, C.; Ulrich, G.; Ziessel, R. Org. Lett. 2006 8, 4445-4448.
7. Goze, C.; Ulrich, G.; Ziessel, R. J. Org. Chem. 2007 72, 313-322.
8. Harriman, A.; Izzet, G.; Ziessel, R. J. Am. Chem. Soc. 2006 128, 10868-10875.
9. Ulrich, G.; Goze, C.; Guardigli, M.; Roda, A.; Ziessel, R. Angew. Chem., Int. Ed. 2005 44, 3694-3698.
10. Gabe, Y.; Ueno, T.; Urano, Y.; Kojima, H.; Nagano, T. Anal. Bioanal. Chem. 2006 386, 621-626.
11. Hiroyuki, S.; Yojiro, K.; Tsutayoshi, M.; Keisuke, T. Japanese patent 11043491, 1999.
12. Kim, H.; Burghart, A.; Welch, M. B.; Reibenspies, J.; Burgess, K. Chem. Commun. 1999, 1889-1890.
13. Tahtaoui, C.; Thomas, C.; Rohmer, F.; Klotz, P.; Duportail, G.; Mely, Y.; Bonnet, D.; Hibert, M. J. Org. Chem. 2007 72, 269-272.
14. Bonnier, C.; Piers, W. E.; Parvez, M.; Sorensen, T. S. Chem. Commun. 2008, 4593-4595.
15. Hudnall, T. W.; Gabbai, F. P. Chem. Commun. 2008, 4596-4597.
16. Wu, L.; Burgess, K. Chem. Commun. 2008, 4933-4935.
17. Wood, T. E.; Thompson, A. Chem. Rev. 2007 107, 1831-1861.
18. Sáez Díaz, R. I.; Bennett, S. M.; Thompson, A. ChemMedChem 2009 4, 742-745.
19. Tamaru, S.; Yu, L. H.; Youngblood, W. J.; Muthukumaran, K.; Taniguchi, M.; Lindsey, J. S. J. Org. Chem. 2004 69, 765-777.
20. Liras, M.; Banuelos Prieto, J.; Pintado-Sierra, M.; Garcia-Moreno, I.; Costela, A.; Infantes, L.; Sastre, R.; Amat-Guerri, F. Org. Lett. 2007 9, 4183-4186.
21. Höpfl, H. In Group 13 Chemistry I: Fundamental New Developments; Mingos, D. M. P., Ed.; Springer-Verlag: Duesseldorf, Germany, 2002; Vol.103, pp 1-56.
22. Beshara, C. S.; Pearce, B. M.; Thompson, A. Can. J. Chem. 2008 10, 951-957.
23. Al-Sheikh Ali, A.; Cipot-Wechsler, J.; Cameron, T. S.; Thompson, A. J. Org. Chem. 2009 74, 2866-2869.
24. Feng, X.; Senge, M. O. J. Chem. Soc., Perkin Trans. 1 2001, 1030-1038.
25. Senge, M. O. Acc. Chem. Res. 2005 38, 733-743.
26. Ulrich, G.; Goze, C.; Goeb, S.; Retailleau, P.; Ziessel, R. New J. Chem. 2006 30, 982-986.