| As a kind of important nitrogen-containing heterocyclic alkaloid,indole and its derivatives are widely present in natural products and drug molecules.They also play an important role in the fields of plants,animals,and human health.Therefore,the highly efficient construction and late-stage functionalization of indoles have attracted significant interesting from a lot of organic and medical chemists.In the periodic table,the fluorine element is the most electronegative one.Due to their excellent properties,fluorine-containing compounds play an important role in aerospace,defense and military areas.Meanwhile,many fluorine-containing substances usually have good biological activities,and they are widely used in medicines and agrochemicals.In addition,as a strong electron-withdrawing group,trifluoromethyl has high stability and good liposolubility.The introduction of trifluoromethyl into organic molecules can often change their physical and chemical properties and improve their biological activities and pharmaceutical efficacies.Thus,the synthesis of fluorinated indole derivatives has important theoretical research value and practical application prospects.This dissertation has developed a series of efficient synthetic methods for fluorinated indole derivatives,including the following three parts:(1).A rhodium-catalyzed regioselective oxidative annulation of indole carboxylic acids and trifluoromethyl substituted aryl internal alkynes was developed for preparation of trifluoromethyl substituted indolopyrone compounds.This method utilized fluorine-containing building block strategy,and it owned several advantages,including simple and easily available starting materials,mild reaction conditions,and good functional group tolerance,etc.(2).An efficient method for assembly of trifluoromethyl substituted indolopyrone-Ir(Ⅰ)metal complexes was developed under mild conditions.A series of Ir(Ⅰ)complexes were successfully prepared with high yield and selectivity.(3).Under metal-free condition,a tandem decarboxylation and fluoride acylation reaction of indole carboxylic acid was achieved in fluoride carboxylic acid solvent.This catalytic system was practical and easy operation,providing a new method for the efficient synthesis of indole-3-fluoroketone compounds. |
