Computational study of solvent effect on ruthenium catalyzed click synthesis of 1,2,3-triazoles

In this study, ruthenium catalyzedazide-alkyne cycloaddition reaction mechanism has been modeled byquantum mechanical methods. In this respect, we have investigated regioselectivity in azide-alkyne reaction on thepresence of ruthenium catalysts in solution phases. Density functional theory and polarized continuum model wereutilized to demonstrate that 1,5-disubstituted triazole is the main product. We demonstrated that the presence ofCp*RuCl(PH3)2 catalyst has an important role on the energy barriers of transition states and so the regioselectivebehavior of synthesis. The thermodynamic stability of Ru-azide-alkyne complexes in transition state structures wascomparatively evaluated in the presence of solvent. It was shown that the production of 1,5-disubstituted triazoles in1,2-dichloroethane solution is more favorable thermodynamically than dimethylformamide.

کلیدواژه ها:

Ruthenium catalyst ، Disubstituted 1 ، 2 ، 3-triazoles ، Click reaction ، DFT computations ، Polarized continuum model