Synthesis of Fluorine-Containing Tetraarylanthracenes via Ruthenium-Catalyzed C?O or C?F Arylation and their Crystal Structures
Synthesis of Fluorine-Containing Tetraarylanthracenes via Ruthenium-Catalyzed C?O or C?F Arylation and their Crystal Structures
复制标题
钌催化C2O或C2F芳基化合成含氟四芳基蒽及其晶体结构
DOI：
10.1055/s-0036-1590937
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发表时间：
2017
期刊：
影响因子：
2
通讯作者：
Kochi Takuya
中科院分区：
文献类型：
--
作者：
Kakiuchi Fumitoshi;Izumoto Akiko;Kondo Hikaru;Kochi Takuya
使用钌催化的 C-O 或 C-F 芳基硼酸酯芳基化合成了含有多个氟基团的四芳基蒽，并进行了结构和光谱研究。人们发现 RuH2(CO)(PPh3)3 催化的芳香酮的 C-O 芳基化对于引入含有多个氟基团的芳基是有效的。以1,4,5,8-四甲氧基蒽醌为原料，通过C-O芳基化和羰基还原，分两步制备了具有氟化芳基的蒽。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，四芳基蒽上氟基的位置导致晶体堆积结构的显着差异。在固态的荧光光谱中观察到四芳基蒽之间的差异大于在氯仿中的荧光光谱。
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.