Pd-catalyzed Suzuki-miyaura Cross-coupling Of Aromatic Heterocyclic Halide With DABO Borocanes

In this thesis,a series of(hetero)aryl DABO boronates are synthesized by dehydration condensation reaction with(hetero)aryl boronic acids and diethanolamine derivatives.Meanwhile,the reactivity of these DABO boronates has been investigated in Suzuki-Miyaura cross-coupling reaction.The main obtained results are shown as belows:1.Aryl DABO boronates can be obtained from the dehydration of aryl boronic acid with DEA(diethanolamine derivatives)by refluxing in non-polar solvents.Heteroaryl DABO boronates were synthesized at room temperature through the same process.2.A series of heteroaromatic compounds were obtained in moderate to excellent yields via Pa Cl2-catalyzed Suzuki-Miyaura cross-coupling reaction of heteroaryl bromides with aryl DABO boronates in the co-solvent of dioxane and water without additional additives.The reaction of heteroaryl DABO boronates with heteroaryl bromides could also be successfully carried out with the participation of the ligand PPh3.And the cross-coupling reaction of various DABO boronates with heteroaryl chlorides required the combination of X-Phos/TBAB to achieve.3.The experimental results showed that the skeleton of diethanolamines has a significant effect on the reactivity of DABO boronates in Suzuki-Miyaura coupling reaction.When the nitrogen atom of diethanolamine contains an electron donating group,the reactivity of DABO boronates is increased;with the increasing of steric effect on the skeleton of diethanolamine,the reactivity is reduced.