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Synthesis 2009(4): 551-556  
DOI: 10.1055/s-0028-1083335
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Reductive Amination - A Convenient Method for Generating Diverse, Mono-Functionalised 5,10,15,20-Tetraphenyl Porphyrins

Chris Welch, Stephen J. Archibald*, Ross W. Boyle*
Department of Chemistry, University of Hull, Kingston-upon-Hull, East Yorkshire, HU6 7RX, UK
Fax: +44(1482)466410; e-Mail: r.w.boyle@hull.ac.uk;
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Publikationsverlauf

Received 11 August 2008
Publikationsdatum:
27. Januar 2009 (online)

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Abstract

Formylation followed by reductive amination of 5,10,15,20-tetraphenyl porphyrin (TPP) is shown to be a versatile synthetic procedure for monosubstitution of the porphyrin core regiospecifically at one β-position. A diverse range of substituents can be introduced in this way in good yields, including cyclen aza-crown macrocycles.

Key words

porphyrin - substitution - cyclen - amination - regioselective

    References

  • 1a The Porphyrin Handbook   Kadish KM. Smith KM. Guillard R. Academic Press; San Diego: 2000. 
  • 1b Colours of Life   Milgrom LR. Oxford University Press; Oxford: 1997. 
  • 2a Straight SD. Kodis G. Terazono Y. Hambourger M. Moore TA. Moore AL. Gust D. Nat. Nanotechnol.  2008,  3:  280 
    Suche in Google Scholar
  • 2b Gust D. Moore TA. Moore AL. Acc. Chem. Res.  2001,  34:  40 
    Suche in Google Scholar
  • 3 Metalloporphyrins in Catalytic Oxidations   Sheldon RA. Marcel Dekker Inc.; New York: 1994. 
  • 4a MacDonald IJ. Dougherty TJ. J. Porphyrins Phthalocyanines  2001,  5:  105 
    Suche in Google Scholar
  • 4b Sternberg ED. Dolphin D. Bruckner C. Tetrahedron  1998,  54:  4151 
    Suche in Google Scholar
  • 5 Shanmugathasan S. Edwards C. Boyle RW. Tetrahedron  2000,  56:  1025 
    CrossrefSuche in Google Scholar
  • 6 Catalano MM. Crossley MJ. Harding MM. King LG. J. Chem. Soc., Chem. Commun.  1984,  1535 
    Crossref
  • 7a Wijesekera T. Dupre D. Cader MSR. Dolphin D. Bull. Soc. Chim. Fr.  1996,  133:  765 
    Suche in Google Scholar
  • 7b Bhyrappa P. Krishnan V. Inorg. Chem.  1991,  30:  239 
    Suche in Google Scholar
  • 8 Bonfantini EE. Burrell AK. Campbell WM. Crossley MJ. Gosper JJ. Harding MM. Officer DL. Reid DCW. J. Porphyrins Phthalocyanines  2002,  6:  708 
    CrossrefSuche in Google Scholar
  • 9 Lane CF. Synthesis  1975,  135 
    Thieme Connect
  • 10 Williams PA. Fulop V. Garman EF. Saunders NFW. Ferguson SJ. Hajdu J. Nature  1997,  389:  406 
    CrossrefSuche in Google Scholar
  • 11 Tainer JA. Getzoff ED. Richardson JS. Richardson DC. Nature  1983,  306:  284 
    CrossrefSuche in Google Scholar
  • 12 Andrioletti B. Ricard D. Boitrel B. New J. Chem.  1999,  23:  1143 
    CrossrefSuche in Google Scholar
  • 13 Bulach V. Mandon D. Weiss R. Angew. Chem., Int. Ed. Engl.  1991,  30:  572 
    CrossrefSuche in Google Scholar
  • 14 Even P. Boitrel B. Coord. Chem. Rev.  2006,  250:  519 
    CrossrefSuche in Google Scholar
  • 15 Halime Z. Lachkar M. Toupet L. Coutsolelos AG. Boitrel B. J. Chem. Soc., Dalton Trans.  2007,  3684 
  • 16 Murugesan S. Shetty SJ. Srivastava TS. Noronha OPD. Samuel AM. Appl. Radiat. Isot.  2001,  55:  641 
    CrossrefSuche in Google Scholar
  • 17 Li G. Slansky A. Dobhal MP. Goswami LN. Graham A. Chen Y. Kanter P. Alberico RA. Spernyak J. Morgan J. Mazurchuk R. Oseroff A. Grossman Z. Pandey RK. Bioconjugate Chem.  2005,  16:  32 
    CrossrefSuche in Google Scholar
  • 18 Mishra AK. Panwar P. Chopra M. Sharma RK. Chantal J.-F. New J. Chem.  2003,  1054 
    Crossref
  • 19 Dadabhoy A. Faulkner S. Sammes PG. J. Chem. Soc., Perkin Trans. 2  2002,  348 
    Crossref
  • 20 Faulkner S. Pope SJA. J. Am. Chem. Soc.  2003,  125:  10527 
    Suche in Google Scholar