Development Of Aryl Boronic Acids Involved Coupling Reaction And Double Arene Addition Reaction Of Norbornenes

Organoboron compounds are not only widely used in organic synthesis,but also can be used as initiators,kerosene antioxidants,fungicides and anticancer drugs for polymerization.And organic boronic acid compounds are widely used in organic boride.For example,and the most widely used Suzuki coupling reaction is the coupling reaction of aryl or alkyl halide with aryl or alkyl boronic acid.In addition,organic boronic acid can also participate in Heck coupling reaction.Therefore,organic boronic acid is an important basic substance in the coupling reaction.Next we will discuss the coupling of organic boronic acid with different kinds of hybridization type carbon.Our research is mainly about the coupling reaction between aryl boronic acid compounds and different kinds of hybridization type carbon.It is mainly divided into two modules,one is the coupling reaction between aryl halide and aryl boronic acids,the other is the coupling reaction between norbornadiene and its derivatives and aryl boronic acid,and we also explored the application of its products in ortho C-H activation of methoxybenzamides.In the coupling between aryl halide and aryl boronic acids,we mainly explored the coupling reaction of aryl halide with aryl boronic acid without extra transition metal catalysts.We found one of the most suitable reaction conditions are that potassium hydroxide(3.0 equiv)as salt,ethanol(0.2 M)as solvent,and the most suitable temperature is 80 ~oC.In general,we developed one of simpler,more moderate conditions and without additional transition metal of the aryl boronic acid and aryl halide coupling reaction,the reaction in a few hours can speed the completion of the colleges and universities.The other studied mainly about that the coupling of norbornene and its derivatives with aryl boronic acid.In this reaction,the most suitable reaction conditions are that sodium carbonate(3.0 equiv),5%Pd(10 mol%),toluene(0.2 M),and the most suitable temperature is70 ~oC.In general,we also have found a relatively green method to obtain norbornene derivatives,and the yield is also good.And some other compounds were also obtained in this study.Of course,the norbornene derivatives may be used as ligands for further research.Regarding the applicability of this compound,our research group will conduct research in the next study.Perhaps the norbornene derivative is a better ligand compound in a certain reaction.All of these require us to conduct further research.In addition,we also have discovered a novel norbornene derivative mediated,Pd catalyzed selective ortho alkylation of aromatic compounds.This reaction uses a simpler amide compound as a guide group and an inexpensive and readily available alkyl halide as an alkylating agent that can react under a catalytic amount of metal and the reaction requires only oxygen as the sole oxidant.In this study,we have studied that the better ligands have a better catalytic effect on the disubstituted amide alkylation,and the reaction exhibits a stronger functional group tolerance.In addition,we also studied the effect of different additives on the reaction efficiency and product selectivity,and found that the use of norbornene type additives can effectively help the C–H bond activation process of the reaction and can be used as a ligand to participate in the future application of C–H bond activation go with.The method and the ligands of the norbornene derivatives have opened a new door for molecular design and synthesis using the C–H bond activation method in the future.