Towards Nonalternant Nanographenes through Self-Promoted Intramolecular Indenoannulation Cascade by C-F Bond Activation

被引:17
作者
Akhmetov, Vladimir [1 ]
Feofanov, Mikhail [1 ]
Papaianina, Olena [1 ]
Troyanov, Sergey [2 ]
Amsharov, Konstantin [1 ]
机构
[1] Friedrich Alexander Univ Erlangen Nuernberg, Dept Chem & Pharm, Organ Chem 2, Nikolaus Fiebiger Str 10, D-91058 Erlangen, Germany
[2] Moscow MV Lomonosov State Univ, Chem Dept, Moscow 119991, Russia
关键词
aromatization; buckybowls; C-C coupling; C-F activation; indenoannulation; POLYCYCLIC AROMATIC-HYDROCARBONS; FRIEDEL-CRAFTS ARYLATION; RATIONAL SYNTHESIS; BUCKYBOWLS;
D O I
10.1002/chem.201902586
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Large polycyclic aromatic hydrocarbons (PAHs) containing pentagons represent an important class of compounds that are considered to be superior materials in future nano-electronic applications. From this perspective, the development of synthetic approaches to large PAHs and nanographenes (NGs) is a matter of great importance. In this context indenoannulation appears to be the most practical way to introduce pentagons into NGs. Here we report that alumina-mediated C-F bond activation is an attractive tool for the synthesis of non-alternant NGs bearing several pentagons. The unique nature of the reaction leads to a rather counter-intuitive outcome and allows considering each previous aryl-aryl coupling as a promoter of the following one, despite the continuous increase in the strain energy. Thus, the presented strategy combines both facile synthesis and significant yields for large nonalternant PAHs and NGs.
引用
收藏
页码:11609 / 11613
页数:5
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