Synthesis And Reactions Of (Z)-Trifluoromethyl Alkenyl Triflates

It is well-known that introducing fluorine atoms into bioactive molecules can lead to some molecular property changes,most of which have positive effects.Among numerous fluorine-containing compounds,trifluoromethyl group constitutes an important structural motif of many bioactive compounds.Recent years have seen rapid development in triflouromethylation catalyzed by transition metals.In addition,the use of trifluoromethylated building blocks have become widely popular because their mild,easily controllable and more selective reaction conditions help avoid harsh reaction conditions and toxic or expensive fluorinating reagents.Among these building blocks,CF3-containing alkenyl derivatives,a type of very important trifluoromethylated building block for CF3-containing compounds,have attracted much attention from chemical researchers.However,the uses of CF3-containing alkenyl derivatives are limited by their singular reaction type and their complex synthetic route.Herein,in order to provide a simple and more effective way to synthesize CF3-containing functional compounds,it is highly desirable to develop a new,flexible and efficient CF3-containing alkenyl derivatives building block.In this study,a new type of trifluoromethylated building block,(Z)-trifluoromethyl alkenyl triflates,was developed and its reaction properties were explored.1.The trifluoromethylated enol anion,generated by the reaction between alkyl aryl ketones and ethyl trifluoroacetate,was captured when Tf2O was added to the reaction.And the(Z)-trifluoromethyl alkenyl triflates were obtained in good yield by means of one-pot synthesis.2.Using(Z)-trifluoromethyl alkenyl triflates as trifluoromethylated building block,CF3-containing aryl acetylene and CF3-containing benzofuran compounds were synthesized.3.Using(Z)-trifluoromethyl alkenyl triflates as trifluoromethylated building block,CF3-containing aryl acetylene and CF3-containing benzofuran compounds were synthesized.4.An efficient approach to(Z)or(E)-3,3,3-trifluoropropenyl derivatives via Palladium-catalyzed geometrically selective hydrogenation of(Z)-trifluoromethyl alkenyl triflates was developed.5.An efficient approach to CF3-containing allyl azides and alkenyl azides via base-controlled divergent regioselective azidation of trifluoromethyl alkenyl triflates was established.