Palladium catalyzed carbonylation of Br-substituted porphyrins

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 8935-8938

  Vinogradov, Sergei A ^a   Wilson, David F ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; PALLADIUM; PORPHYRIN DERIVATIVE;

ARTICLE; CATALYSIS; DERIVATIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032481008     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02019-X     Document Type: Article

References (23)

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2. 1. Adler, A. D.; Longo, F. R.; Shergalis, W. D. J. Am. Chem. Soc. 1964, 86, 3145-3149; Adler, A. D.; Sklar, L.; Longo, F. R.; Finarelli, J. D.; Finarelli, M. G. Heterocycl. Chem. 1968, 5, 669-678.
3. 2. Lindsey, J. S.; Schreiman, I. C.; Hsu, H. C.; Kearney, P. C.; Marguerettaz, A. M. J. Org. Chem. 1987, 52, 827-836; Lindsey, J. S.; Maccrum, K. A.; Tyhonas, J. S.; Chuang, Y. Y. J. Org. Chem. 1994, 59, 579-587.
4. 2. Lindsey, J. S.; Schreiman, I. C.; Hsu, H. C.; Kearney, P. C.; Marguerettaz, A. M. J. Org. Chem. 1987, 52, 827-836; Lindsey, J. S.; Maccrum, K. A.; Tyhonas, J. S.; Chuang, Y. Y. J. Org. Chem. 1994, 59, 579-587.
5. 3. Vinogradov, S. A.; Wilson, D. F. J. Chem. Soc., Perkin Trans.II 1994, 103-111; Vinogradov, S. A.; Lo, L.-W.; Jenkins, W. T.; Evans, S. M.; Koch, C.; Wilson, D. F. Biophys. J. 1996, 70, 1609-1617.
6. 3. Vinogradov, S. A.; Wilson, D. F. J. Chem. Soc., Perkin Trans.II 1994, 103-111; Vinogradov, S. A.; Lo, L.-W.; Jenkins, W. T.; Evans, S. M.; Koch, C.; Wilson, D. F. Biophys. J. 1996, 70, 1609-1617.
7. 4. Lavi, A.; Johnson, F. M.; Ehrenberg, B. Chem. Phys. Lett. 1994, 231, 144-150.
8. 5. For review see: Kobayashi, N. in Phthalocyanines. Properties and Applications; ed. Leznoff, C. C.; Lever, A. B. P., VCH: New York, 1993; Vol. 2, p.97.
9. 6. The recent work of Cavaleiro et al. [Vicente, M. G. H.; Tome, A. C.; Walter, A.; Cavaleiro, J. A. S. Tetrahedron Lett. 1997, 38, 3639-3642] presents an alternative and promising route to the TBP system, however to date only the synthesis of basic non-substituted tetrabenzoporphyrin has been reported.
10. 7. Khoroshutin, A.V., Vinogradov, S.A., Wilson, D.F, Abstr. Pap. ACS, 215: 49-ORGN, U16-U16 Part 2, Apr 2, 1998.
11. 8. Arnold, D. P.; Nitschinsk, L. J. Tetrahedron 1993, 34, 693-696; DiMagno, S. G.; Lin, V. S. Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983-5993; Chan, K. S.; Zhou, X.; Luo, B. S.; Mak, T. C. W. J. Chem. Soc. Chem. Comm. 1994, 271-272; Ali, H.; Vanlier, J. E. Tetrahedron 1994, 50, 11933-11944.
12. 8. Arnold, D. P.; Nitschinsk, L. J. Tetrahedron 1993, 34, 693-696; DiMagno, S. G.; Lin, V. S. Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983-5993; Chan, K. S.; Zhou, X.; Luo, B. S.; Mak, T. C. W. J. Chem. Soc. Chem. Comm. 1994, 271-272; Ali, H.; Vanlier, J. E. Tetrahedron 1994, 50, 11933-11944.
13. 8. Arnold, D. P.; Nitschinsk, L. J. Tetrahedron 1993, 34, 693-696; DiMagno, S. G.; Lin, V. S. Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983-5993; Chan, K. S.; Zhou, X.; Luo, B. S.; Mak, T. C. W. J. Chem. Soc. Chem. Comm. 1994, 271-272; Ali, H.; Vanlier, J. E. Tetrahedron 1994, 50, 11933-11944.
14. 8. Arnold, D. P.; Nitschinsk, L. J. Tetrahedron 1993, 34, 693-696; DiMagno, S. G.; Lin, V. S. Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983-5993; Chan, K. S.; Zhou, X.; Luo, B. S.; Mak, T. C. W. J. Chem. Soc. Chem. Comm. 1994, 271-272; Ali, H.; Vanlier, J. E. Tetrahedron 1994, 50, 11933-11944.
15. 9. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985, Ch.8, p. 341-451.
16. 2 in 31% yield.
17. 3N) and 20-30 ml of solvent were placed in a pressure resistant glass vial (Ace Glass Inc.), connected to a CO tank by a copper tubing. The vial was immersed in the oil bath and temperature was brought up to the desired value (normally 90-95°C) under continuous stirring and slow flow of CO. The lid of the vial was then tightened and the pressure was raised to 2 atm. The reaction mixture workup involved filtration, removal of the solvent in vacuum and chromatography of the product.
18. max = 425 nm).
19. 13. THF was added to improve the solubility of the substrate.
20. 4Porph (4) as well as analytical and spectroscopic data on all newly synthesized porphyrins are available on request and will be published elsewhere.
21. 15. Vinogradov, S.A., Wilson, D.F. Adv. Exptl. Med. Biol., 1997, 428, 657-662; Vinogradov, S.A., Wilson, D.F. Abstr. Pap. ACS, 215: 50-ORGN, U16-U16 Part 2, Apr 2, 1998.
22. 15. Vinogradov, S.A., Wilson, D.F. Adv. Exptl. Med. Biol., 1997, 428, 657-662; Vinogradov, S.A., Wilson, D.F. Abstr. Pap. ACS, 215: 50-ORGN, U16-U16 Part 2, Apr 2, 1998.
23. 2 in DMF.