Oxidative two-way regiocontrolled coupling of 3-methoxycarbonylcatechol and indoles to arylindoles.

Yoshinari SawamaShoko KuwataMiyu MaeTaro Udagawa Shuji Akai Hironao Sajiki

Published in: Chemical communications (Cambridge, England) (2022)

3-Methoxycarbonylcatechol effectively underwent two-way regiocontrolled coupling with indoles via an ortho -benzoquinone intermediate, resulting from phenyliodine(III) diacetate oxidation, to generate 4-adducts or 5-adducts with or without BF 3 ·Et 2 O in a one-pot manner. DFT calculations confirmed the obtained regioselectivities.

Keyphrases

density functional theory
room temperature
electron transfer
molecular dynamics
molecular dynamics simulations
hydrogen peroxide
molecular docking
nitric oxide
monte carlo