The Synthesis Of Alkylboronic Esters And Application Of Alkylboronic Esters In Suzuki—Miyaura Cross-Coupling Reaction

C-C, C-X bond construction is very important for organic synthesis. The Suzuki-Miyaura cross-coupling as a popular method in synthesis arises. Since Suzuki first reported the cross-coupling, many groups have studied Suzuki-Miyaura cross-coupling and have made significant achievements, include the improvement of ligands, catalysts, solvents and so on. However the synthesis of organic boron reagents and the application of alkylboronic esters in Suzuki-Miyaura cross-coupling were seldom reported.In the chapter 2 of this dissertation, we studied the cross-coupling of alkyl halides and diboron reagent. Through the method we got alkylboronic esters successfully. It was fund that the combination of Cu I/Dimethylglycine /t-Bu OLi/DMF gave the best yield. Under the condition, several alkyl halides with functional groups were converted into the products in good yield. The primary and secondary alkyl halides also gave good yield.In the chapter 3 of this dissertation, the cross-coupling of alkylboronic esters and aryl iodides was investigated. After screening ligands, catalysts, temperature and solvents, we got the optimized reaction condition for this reaction was using Pd(OAc)2 /PPh3 /t-Bu OLi /Nitrobenzene /DMF. However, the aryl iodides with electron-withdrawing groups couldn’t give the products.In the chapter 4 of this dissertation, we studied the the dimerization of 1-phenethyl bromide. We found that the diboron reagent could promote the homocoupling reaction of 1-phenethyl bromide. Using the reaction condition several aryl halides were tested. Only 1-phenethyl halides could gave homocoupling pruducts.