Abstract
The reaction mechanism of Pd2+-catalyzed regioselective C-H alkylation of indole with MesICH2CF3OTf 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 find that the C-H activation step was realized by the acetate anion (-OAc) assisted concerted metalation deprotonation (CMD) process and the transition state of C-H activation process is a square planar configuration. Moreover, the calculation results suggest that the regioselectivity of C-H bond alkylation of indole with MesICH2CF3OTf can be ascribed to the different stability of the CMD transition states in C-H activation step and the relative stabilities of deprotonated intermediates.
Highlights
Indole and its derivatives as one kind of privileged and significant N-heterocycles have been widely found in a variety of natural products and drugs.[1]
We find 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 configuration
The detailed reaction mechanism of Pd(II)-catalyzed regioselective C-H alkylation of indole with MesICH2CF3OTf is scrupulously explored by our computational studies
Summary
Indole and its derivatives as one kind of privileged and significant N-heterocycles have been widely found in a variety of natural products and drugs.[1]. In recent years the introduction of fluoroalkylated groups into organic compounds has become very popular due to it often exhibits potential pharmaceutical applications.[5]
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