Facile peripheral functionalization of porphyrins by Pd-catalyzed [3+2] annulation with alkynes

被引：59
|
作者：
Sahoo, Akhila K.
Mori, Shigeki
Shinokubo, Hiroshi [1 ]
Osuka, Atsuhiro
机构：
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
[2] Kyoto Univ, IIC, JST, PRESTO,Sakyo Ku, Kyoto 6068502, Japan
[3] Kyoto Univ, IIC, JST, CREST,Sakyo Ku, Kyoto 6068502, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 47期
关键词：
alkynes; fused-ring systems; oxidation; palladium; porphyrinoids;
D O I：
10.1002/anie.200603580
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Going round the outside: The palladium-catalyzed coupling of meso-bromoporphyrins with a variety of internal alkynes efficiently provides peripherally cyclopentadiene-fused porphyrins. This modification has a significant impact on the electronic system of the porphyrin rings (see scheme), which results in non-porphyrin-like absorption spectra and narrower HOMO-LUMO gaps. Oxidation of the outer C=C bond is facilitated by the induced strain. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：7972 / 7975
页数：4
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