Institut für Organische Chemie , Universität Würzburg , Am Hubland , 97074 Würzburg , Germany.
Center for Nanosystems Chemistry (CNC) , Universität Würzburg , Theodor-Boveri-Weg , 97074 Würzburg , Germany.
J Org Chem. 2018 May 18;83(10):5339-5346. doi: 10.1021/acs.joc.8b00301. Epub 2018 Mar 20.
Here we report a general method for the synthesis of polycyclic aromatic dicarboximides (PADIs) by palladium-catalyzed annulation of naphthalene dicarboximide to different types of aromatic substrates. Reaction conditions were optimized by systematic variation of ligand, solvent, and additive. It was shown that solvent has a decisive effect on the yield of the reaction products, and thus 1-chloronaphthalene as solvent afforded the highest yield. By applying the optimized reaction conditions, a broad series of planar carbo- and heterocycle containing PADIs were synthesized in up to 97% yield. Moreover, this approach could be applied to curved aromatic scaffold to achieve the respective bowl-shaped PADI. Two-fold annulation was accomplished by employing arene diboronic esters, affording polycyclic aromatic bis(dicarboximides). The optical and electrochemical properties of this broad series of PADIs were explored as well.
在这里，我们报告了一种通过钯催化萘二酰亚胺与不同类型芳香底物的环化反应合成多环芳烃二酰亚胺（PADIs）的通用方法。通过系统改变配体、溶剂和添加剂来优化反应条件。结果表明，溶剂对反应产物的收率有决定性的影响，因此以 1-氯萘作为溶剂可以获得最高的收率。通过应用优化的反应条件，可以高达 97%的收率合成了广泛的含有平面碳环和杂环的 PADI。此外，该方法可应用于弯曲芳香支架以实现各自的碗状 PADI。通过使用芳烃二硼酸酯完成了两倍环化反应，得到了多环芳烃双（二酰亚胺）。还研究了这一系列广泛的 PADI 的光学和电化学性质。
