An Extremely Simple Dibenzopentalene Synthesis from 2-Bromo-1-ethynylbenzenes Using Nickel(0) Complexes: Construction of Its Derivatives with Various Functionalities
An Extremely Simple Dibenzopentalene Synthesis from 2-Bromo-1-ethynylbenzenes Using Nickel(0) Complexes: Construction of Its Derivatives with Various Functionalities
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DOI：
10.1002/chem.200802471
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发表时间：
2009-01-01
影响因子：
4.3
通讯作者：
Kubo, Takashi
中科院分区：
文献类型：
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作者：
Kawase, Takeshi;Konishi, Akihito;Kubo, Takashi
用镍(0)络合物从易得的2-溴-1-乙炔基苯合成了一种极其简单的二苯并戊烯。虽然产率适中，但一步形成三个C-C键和起始原料的高可用性是该反应的重要优势。作为重要中间体的芳基镍(II)配合物以相对稳定的晶体形式被分离出来，其结构经X-射线单晶分析得到确证。的高度稳定性。这种络合物应该在这一反应中发挥关键作用。该反应适用于制备具有各种官能团的二苯并戊烯。它们的电子性质与理论计算一致。这些化合物的循环伏安曲线显示出高度的两性氧化还原性质。特别是，四甲氧基衍生物的给电子性能比低聚硫吩类和二苯并二硫吩类要大，几乎可以与并五苯类化合物相媲美。
An extremely simple dibenzopentalene synthesis from readily available 2-bromo-1-ethynylbenzenes using a nickel(0) complex is described. Although the yields are moderate, the formation of three C-C bonds in a single process and the high availability of the starting materials are important advantages of this reaction. The corresponding aryl-nickel(II) complex as ail important intermediate was isolated as relatively stable crystals, and the structure was confirmed b X-ray crystallographic analysis. The high stability of. this complex should play a key role in this reaction. The reaction is applicable to the preparation of dibenzopentalenes bearing various functional groups. Their electronic properties are consistent with theoretical calculations. The cyclic voltammograms of these compounds reveal highly amphoteric redox properties. In particular, the electron-donating property of a tetramethoxy derivative is greater than that of oligothiophenes and dibenzodithiophenes and almost comparable to that of pentacene.