PDF herunterladen
Synthesis 2009(1): 59-61  
DOI: 10.1055/s-0028-1083267
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Norbornane-Bridged Diporphyrins via Palladium-Catalyzed [3+2] Annulation Strategy

Masatoshi Mizumura, Hiroshi Shinokubo*, Atsuhiro Osuka*
Department of Chemistry, Graduate School of Science, Kyoto University, Kyoto 606-8502, Japan
Fax: Fax: +81(75)7533970; e-Mail: hshino@apchem.nagoya-u.ac.jp; e-Mail: osuka@kuchem.kyoto-u.ac.jp;
Weitere Informationen

Publikationsverlauf

Received 24 October 2008
Publikationsdatum:
12. Dezember 2008 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

The reaction of meso-bromoporphyrins with norbornene-fused porphyrins afforded novel norbornane-bridged diporphyrins in excellent yields via palladium-catalyzed [3+2] annulation reaction.

Key words

alkenes - annulation - catalysis - palladium - porphyrins

    References

  • For reviews, see:
  • 2a Sharman WM. van Lier JE. J. Porphyrins Phthalocyanines  2000,  4:  441 
    Google Scholar
  • 2b Setsune J. J. Porphyrins Phthalocyanines  2004,  8:  93 
    Google Scholar
  • 3 Locos OB. Arnold DP. Org. Biomol. Chem.  2006,  4:  902 
    CrossrefGoogle Scholar
  • 4a Sahoo AK. Mori S. Shinokubo H. Osuka A. Angew. Chem. Int. Ed.  2006,  45:  7972 
    Google Scholar
  • 4b Mizumura M. Shinokubo H. Osuka A. Angew. Chem. Int. Ed.  2008,  47:  5387 
    Google Scholar
  • 5a Grigg R. Kennewell P. Teasdale A. Sridharan V. Tetrahedron Lett.  1993,  34:  153 
    Google Scholar
  • 5b Pletnev AA. Tian Q. Larock RC. J. Org. Chem.  2002,  67:  9276 
    Google Scholar
  • 5c Catellani M. Del Rio A. Russ. Chem. Bull.  1998,  47:  928 
    Google Scholar
  • 5d Saito K. Katsuhiko O. Sano M. Kiso S. Takeda T. Heterocycles  2002,  57:  1781 
    Google Scholar
  • 5e Lautens M. Hulcoop DG. J. Org. Chem.  2001,  66:  8217 
    Google Scholar
  • 5f Hulcoop DG. Lautens M. Org. Lett.  2007,  9:  1761 
    Google Scholar
1

Present address: Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8603, Japan.

6

Crystal data of 3CuCu meso : C131H145N8Cu2, M w  = 1958.63, triclinic, space group P 1 (No. 2), a = 17.253 (5) Å, b = 19.793 (5) Å, c = 24.020 (7) Å, α = 113.578 (8)˚, β = 90.923 (12)˚, γ = 95.734 (12)˚, V = 6919 (3) ų, Z = 2, D calc = 0.940 g/cm³, T = 123 (2) K, 49358 measured reflections, 22773 unique reflections, R = 0.0958 [I > 2.0σ(I)], wR = 0.3010 (all data), GOF = 0.943 [I > 2.0σ(I)].