Theoretical studies on the mechanism of Pd2+-catalyzed regioselective C-H alkylation of indole with MesICH2CF3OTf

Abstract

The reaction mechanism of Pd 2+ -catalyzed regioselective C-H alkylation of indole with MesICH 2 CF OTf has been investigated by the density functional theory calculations. The reaction mechanism mainly contains four steps C-H activation, oxidative addition, reductive elimination and ligands substitution.From our calculations, we nd that the C-H activation step was realized by the acetate anion ( -OAc) assisted CMD process and the transition state of C-H activation process is a square planar con guration. Moreover, the calculation results suggest that the regioselectivity of C-H bond alkylation of indole with MesICH 2 CF 3 OTf can be ascribed to the different stability of the CMD transition states in C-H activation step and different acidities of C-H bonds.