Construction of multiporphyrin arrays via selective cross-metathesis

Organic Letters

Volumn 8, Issue 12, 2006, Pages 2595-2598

  Langford, Steven J ^a   Latter, Melissa J ^a   Woodward, Clint P ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33745548552     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060867n     Document Type: Article

References (28)

1. Some recent topical reviews include: (a) Imahori, H. J. Phys. Chem. B 2004, 108, 6130.
2. (b) Drain, C. M.; Hupp, J. T.; Suslick, K. S.; Wasielewski, M. R. J. Porph. Phthal. 2002, 6, 243.
3. (c) Imahori, H. Org. Biomol. Chem. 2004, 2, 1425.
4. (d) Satake, A.; Kobuke, Y. Tetrahedron 2005, 61, 13.
5. (a) Burrell, A. K.; Officer, D. L.; Plieger, P. G.; Reid, D. C. W. Chem. Rev. 2001, 101, 2751 and references therein.
6. (b) Frampton, M. J.; Akdas, H.; Cowley, A. R.; Rogers, J. E.; Slagle, J. E.; Fleitz, P. A.; Drobizhev, M.; Rebane, A.; Anderson, H. L. Org. Lett. 2005, 7, 5365.
7. (c) Arnold D. P. Synlett 2000, 296.
8. Liu, X.; Sternberg, E.; Dolphin, D. Chem. Commun. 2004, 57, 852.
9. (a) Kim, Y.; Mayer, M. F.; Zimmerman, S. C. Angew. Chem., Int. Ed. 2003, 42, 1121.
10. (b) van Gerven, P. C. M.; Johannes, J. A. A. W.; Gerritsen, J. W.; Speller, S.; Nolte, R. J. M.; Rowan, A. E. Chem. Commun. 2005, 28, 3535.
11. (c) Ikeda, C.; Satake, A.; Kobuke, Y. Org. Lett. 2003, 5, 4935.
12. (d) Cao, Y.; Wang, L.; Bolt, M.; Vysotsky, M. O.; Bohmer, V. Chem. Commun. 2005, 58, 3132.
13. (e) Guidry, E. N.; Cantrill, S. J.; Stoddart, J. F.; Grubbs, R. H. Org. Lett. 2005, 7, 2129.
14. (f) Bakker, J. M.; Langford, S. J.; Latter, M. J.; Lee, K. A.; Woodward, C. P. Aust. J. Chem. 2005, 58, 757.
15. This is especially important in regioselective mixed metalloporphyrins systems, which are otherwised formed through statistical metalations post-multiporphyrin synthesis.
16. Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
17. This procedure has obvious uses with other olefins. For example, we have reacted 3 with allylglycine, which acts like a type-II olefin, to form a porphyrin α-amino acid in good yield. Conversely, we have reacted type-I olefins such as resin-bound undecenoate esters with protoporphyrin IX, which in our hands acts as a type-III olefin. These results and their applications will be published at a later date.
18. Adler, A. D.; Longo, F. R.; Finarelli, J. D.; Goldmacher, J.; Assour, J.; Korsakoff, L. J. Org. Chem. 1967, 32, 476.
19. Mainly tetra(p-methoxyphenyl)porphyrin and only a small amount of the desired monobutenyl porphyrin 2 was isolated using a 3:1 aldehyde ratio due to the greater reactivity of the p-methoxybenzaldehyde under the conditions used.
20. Buchler, J. W. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 1A, p 389.
21. The lower yield observed for carboxylic acids over esters in CM has been recently discussed; see: Elaridi, J.; Jackson, W. R.; Robinson, A. J. Tetrahedron: Asymmetry 2005, 16, 2025.
22. The acrylate porphyrin 10 was produced in 84% yield by reaction of an acrylate ester and 5,10,15-tris(p-tolyl)-20-(p-hydroxyphenyl)porphyrin. See: Nowakowska, M.; Karewicz, A.; Loukine, N.; Guillet, J. E. Polymer 2002, 43, 2003.
23. The alternative synthesis of 1 employing an esterification procedure by reacting 5 or 6 and 5,10,15-tris(p-tolyl)-20-(p-hydroxyphenyl)porphyrin leads to in situ demetalation of the metalloporphyrin.
24. The reduced yields are thought to result from the formation of a coordination product between catalyst 7 and porphyrin 4.
25. Previous reports on the reduction of alkyne porphyrins utilized palladium on carbon in THF with good effect; see: Bampos, N.; Marvaud, V.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 335.
26. The success of the hydrogenation is important in instances where both geometric isomers are formed by CM. While not yet attempted, this last result opens up the possiblify of performing a CM/hydrogenation tandem reaction to produce flexibly linked porphyrin systems in one pot.
27. -11. Crystallographic data for the structure analyses have been deposited with the Cambridge Crystallographic Data Centre, CCDC 603983 for structure of 12. Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge, CB21EZ, UK (fax: +44-1223-336-033; e-mail: deposit@ccdc.cam.ac.uk or http://www.ccdc.cam.ac.uk).
28. The formation of oligomers of 13 is possibile and no doubt contributes to the reduced yield obtained. For a previous study in this regard, see ref 4b.