Synthesis of carbon-carbon linked porphyrinoligomers by utilization of Heck-type coupling of natural tetrapyrroles

Tetrahedron Letters

Volumn 38, Issue 2, 1997, Pages 223-224

  Gauler, Rainer ^a   Risch, Nikolaus ^a  

^a UNIVERSITY OF PADERBORN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0031021690     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02280-0     Document Type: Article

References (10)

1. A. K. Burrell, D. L. Officer, D. C. W. Reid, Angew. Chem. Int. Ed. Engl. 1995, 34, 900-902.
2. Pandey, K. M. Smith, T.J. Dougherty, J. Med. Chem. 1990, 33, 2032-2038.
3. (a) H. Ali, J. E. van Lier, Tetrahedron 1994, 50, 11933-11944;
4. (b) D. P. Arnold, L. J. Nitschinsk, Tetrahedron Lett. 1993, 34, 693-696;
5. (c) K. S. Chang., B. Luo, T. C. Mak, J. Chem. Soc., Chem. Commun. 1994, 271-272.
6. T. Jeffrey, J. Chem. Soc., Chem. Commun. 1984, 1287-1289.
7. The conditions of the coupling reaction: 1 mmol bromoporphyrin was heated at 85 °C with 1 mmol alkene, 1 mmol tetra-n-butyl-ammonium bromide, 5 mmol potassium carbonate, 1 mmol lithium chloride 0.05 mmol palladium(II)-acetate in 10 ml DMF for 8 to 15 h.
8. Synthesis of the regioisomers 1a, 1b see: R. Bonnett, I. H. Campion-Smith, A. N. Kozyrev, A. F. Mironov, J. Chem. Research 1990, 138-139. To our surprise, repeated crystallisation from dichloromethane : hexane (5:1) yielded in regioisomerically pure bromodeuteroporphyrin 1, which could not yet be assigned as either the 3-or 8-regioisomer. (In all schemes, we tentatively present those regioisomers substituted at C-8.)
9. 2): λ (1g ε)= 595 (4.771), 549 (4.603), 413 (5.161).
10. max (lg ε)= 589 (4.873), 547 (4.809), 510 (4.243), 413 (5.598).