Akhmetov Vladimir, Feofanov Mikhail, Papaianina Olena, Troyanov Sergey, Amsharov Konstantin
Department of Chemistry and Pharmacy, Organic Chemistry II, Friedrich-Alexander University Erlangen-Nuernberg, Nikolaus-Fiebiger Str. 10, 91058, Erlangen, Germany.
Chemistry Department, Moscow State University, Leninskie gory, 119991, Moscow, Russia.
Chemistry. 2019 Sep 6;25(50):11609-11613. doi: 10.1002/chem.201902586. Epub 2019 Aug 7.
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.
含有五元环的大型多环芳烃（PAHs）是一类重要的化合物，被认为是未来纳米电子应用中的优质材料。从这个角度来看，开发大型PAHs和纳米石墨烯（NGs）的合成方法至关重要。在这种情况下，茚并化似乎是将五元环引入NGs的最实用方法。在此，我们报道氧化铝介导的C-F键活化是合成含有多个五元环的非交替型NGs的一种有吸引力的工具。该反应的独特性质导致了一个相当违反直觉的结果，并且尽管应变能不断增加，但可以将之前的每一次芳基-芳基偶联视为后续偶联的促进剂。因此，所提出的策略结合了大型非交替型PAHs和NGs的简便合成方法以及高收率。
