Abstract
Promising results of an efficient and convenient strategy for the annulation of polycyclic aromatic compounds (PACs), employing orthoquinones as starting material and comprising allylation, pinacol rearrangement, ring-closing metathesis (RCM), and one-pot reduction followed by Wagner-Meerwein rearrangement, are presented. The strategy involves introducing triallylborane prepared in situ in the allylation step. Moreover, a novel expedient method for the preparation of 9,10-diallylphenanthrene was introduced.
Highlights
Polycyclic aromatic compounds (PACs) have attracted particular interest because of their unique chemical and physical properties and promising applications in organic electronics, such as light-emitting diodes (LEDs), field-effect transistors (FETs), and photovoltaic cells [1,2,3,4]
The development and elaboration of effective strategies for the preparation of polycyclic aromatic compounds (PACs) remain of significance [5]
The most popular synthetic strategies start from simple aromatic precursors and exploit oxidative aromatic coupling as the key step leading to fused aromatic systems [6,7,8,9,10,11]
Summary
Polycyclic aromatic compounds (PACs) have attracted particular interest because of their unique chemical and physical properties and promising applications in organic electronics, such as light-emitting diodes (LEDs), field-effect transistors (FETs), and photovoltaic cells [1,2,3,4]. The most popular synthetic strategies start from simple aromatic precursors ( with substituents) and exploit oxidative aromatic coupling as the key step leading to fused aromatic systems [6,7,8,9,10,11]. This approach is usually limited to reasonably electron-rich aromatic systems
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