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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;
Further Information

Publication History

Received 24 October 2008
Publication Date:
12 December 2008 (online)

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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

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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)].