Study On Fluorinated Difunctional Reaction Of Olefins

In recent years,fluorine substituents have been increasingly used in pharmaceuticals and agrochemicals,as well as in materials science due to their ability to regulate the p Ka of molecules,alter the acidity and alkalinity of nearby groups,increase the lipophilicity of molecules,and provide metabolic stability and bioavailability.And thus more and more researchers pay attention and favor in this filed.Now,there are varieties of methods to introduce fluorine atoms into a molecule,including different ways to build the aryl C-F,alkyl C-F,and the fluorination of unsaturated double bonds.In which the fluorination of unsaturated double bonds are not only able to introduction of a fluorine atom can also be favored by introducing other useful groups into the molecule.More and more scientific researchers have tried this way to synthesize valuable products.According to reports,the fluorination of unsaturated double bonds that has been achieved now,there are oxyfluorination,aminofluorination,hydrofluorination,carbofluorination,phosphonofluorination and difluorination,sulfonation fluorination,etc.,but this area still contains many undiscovered progress.Alkyl carboxylic acids are often used as alkyl synthons in various types of coupling reactions in recent years,not only because of their low cost and availability,but also because they are relatively stable and easy to form alkyl radicals.Such decarboxylation reactions are usually achieved by the catalysis of transition metals,including silver catalytic,photocatalytic and other metals such as palladium,copper,manganese,etc.And here we have present the first report of alkylfluoroation of unsaturated double bonds,which was achieved under the silver-catalyzed conditions,the select fluorine reagents act as oxidants and fluorine sources.In this reaction,AgNO₃ react with selective fluorine reagents to form oxidized trivalent silver ions,then the carboxylic acid generates alkyl radicals with one carbon atom removed.Next the radicals attack the unsaturated double bonds of alkene,finally the intermediate attacked by fluoride ions to produce alkylfluorination products.These reaction conditions are mild,operating simply and can be achieved directly at room temperature.They are not only suitable for activating olefins but also for non-activated olefins.In addition,the reaction has a wide range of functional group compatibility,whether it is alkene substrates or alkyl carboxylic acid substrates.