C-F Bond Functionalization Of Unactivated Aryl Fluorides

In recent years,research on inert chemical bonds(C-H,C-C,C-O,C-F,etc.)has been a hot topic.Inert fluorocarbon bonds are high in energy and difficult to activate,which is a big challenge for us and has great scientific significance.Fluorine compounds are well known in pharmaceutical chemistry,materials chemistry,and life sciences.We modify fluorochemicals by C-F bond activation.Therefore,it is of high academic as well as practical value to research on the activation of fluorocarbon bonds.This thesis first we mainly discuss about the coupling reaction of fluoroaromatic inert carbon-carbon bond cleavage with various reagents,transition metal-catalyzed C-H activation reaction and coupling reaction of fluorinated aromatic hydrocarbons and C-H compounds.Secondly,we use fluorinated aromatic hydrocarbons as electrophiles,benzoxazole as nucleophilic reagent,and nickel as catalyst to realize C-F and C-H activation to synthesize aryl-heteroaryl biaryl compounds.Finally,what is described is that the progress of the Heck reaction of fluorinated aromatic hydrocarbons.On all accounts,the following results have been achieved:1.A nickel-catalyzed coupling reaction of an inert fluoroaromatic hydrocarbon with an oxazole is achieved.This conversion provides a simple and efficient synthesis for breaking the C-F bond and introducing the oxazole group.Through this method,an important natural product anti-tuberculosis drug texaline can be synthesized simply and efficiently.2.We first use nickel to catalyze the Heck reaction of the carbon-fluorine bond,which is optimized to improve the yield.Finally,the carbene-catalyzed fluorocarbon Heck reaction was found and the yield was well,but the substrate was not highly applicable.