pinpoint- 氟代菲：新的合成方法和溶解度增强策略。
Pinpoint-fluorinated phenacenes: new synthesis and solubility enhancement strategies.
机构信息
Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba , Tsukuba, Ibaraki 305-8571, Japan.
出版信息
Org Lett. 2015 Mar 6;17(5):1126-9. doi: 10.1021/ol503759d. Epub 2015 Feb 16.
The Pd(II)-catalyzed cyclizations of 2,2-difluorovinylated biaryls, following a Friedel-Crafts-type mechanism, provide a new route to pinpoint-fluorinated phenacenes. The single fluorine substituent stabilized the synthesized fluoropicenes (fluoro[5]phenacenes) toward aerial oxidation and contributed to their solubility in organic solvents. For example, 6- and 13-fluoropicenes were 25- and 15-fold more soluble in THF than nonfluorinated picene. X-ray crystal structure analysis revealed that the fluorine substituent did not alter molecular planarity.
Pd(II)催化的 2,2-二氟乙烯基联苯环化反应，遵循Friedel-Crafts 型反应机理，为 pinpoint-氟代菲提供了一条新途径。单氟取代基稳定了合成的氟代菲（氟代[5]菲），使其不易被氧化，并增加了其在有机溶剂中的溶解度。例如，6-和 13-氟代菲在 THF 中的溶解度比非氟代菲分别高出 25 倍和 15 倍。X 射线晶体结构分析表明，氟取代基并没有改变分子的平面性。
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