Tetraarylanthracenes containing several fluoro groups were synthesized using the ruthenium-catalyzed C–O or C–F arylation with arylboronates and their structural and spectroscopic studies were conducted. The RuH2(CO)(PPh3)3-catalyzed C–O arylation of aromatic ketones was found to be effective for the introduction of aryl groups containing multiple fluoro groups. Anthracenes possessing fluorinated aryl groups were prepared in two steps from 1,4,5,8-tetramethoxyanthraquinone by C–O arylation and reduction of the carbonyl groups. A tetraphenylanthracene containing a fluorinated anthracene moiety was also prepared using C–F phenylation of octafluoroanthraquinone. Single-crystal X-ray diffraction analysis showed that the positions of fluoro groups on the tetraarylanthracenes lead to notable difference in the crystal packing structures. The larger difference between the tetraarylanthracenes was observed in the fluorescence spectra in the solid state than those in chloroform.

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钌催化C-O或C-F芳基化合成含氟四芳基蒽及其晶体结构

使用钌催化的 C-O 或 C-F 芳基化与芳基硼酸酯合成了含有几个氟基团的四芳基蒽，并进行了它们的结构和光谱研究。发现 RuH2(CO)(PPh3)3 催化的芳族酮的 C-O 芳基化可有效引入含有多个氟基团的芳基。具有氟化芳基的蒽由 1,4,5,8-四甲氧基蒽醌通过 C-O 芳基化和羰基的还原分两步制备。还使用八氟蒽醌的 C-F 苯基化制备了含有氟化蒽部分的四苯基蒽。单晶X射线衍射分析表明，四芳基蒽上氟基团的位置导致晶体堆积结构的显着差异。