Synthesis of Bifunctional Boron-Lewis Acids - Thorough Investigation of the Adduct Formation with Pyrimidine

Three bifunctional boron-Lewis acids based on a 1,2-diethynylbenzene backbone were synthesized using a tin-boron exchange protocol in good to very good yields. Complexation experiments with pyrimidine were thoroughly investigated using the example of 1,2-bis(benzo[d][1,3,2]dioxaborol-2-ylethynyl)benzene (3) in solution, in the solid phase and by quantum-chemical calculations. Two adducts were structurally investigated by X-ray diffraction experiments. DOSY-/VT-NMR experiments gave insight into the dynamic behaviour of the synthesized poly-Lewis acids with pyrimidine.

Automated summary

In this study, three bifunctional boron-Lewis acids were synthesized using a tin-boron exchange protocol, and the complexation reaction between these acids and pyrimidine was thoroughly investigated. The results revealed the dynamic behavior between the synthesized acids and pyrimidine.