Pd-Catalyzed C-7 Arylation of Indolines with Aryltriazenes under Mild Conditions
Jianan Gao, Qinglang Song, Lin Zhang, Junhao Shao, Bin Wang, Azhar Iqbal, Weiwei Jin, Yu Xia, Chenjiang Liu, Yonghong Zhang
Abstract
A palladium-catalyzed direct C–H arylation of indolines at C-7 position has been achieved at near-ambient temperature. The reaction was carried out with aryltriazene as a stable aryl source and electron shuttle to sustainably release aryl radical in situ under the action of promoter, and pyrimidine as a detachable directing group for the synthesis of 7-arylindolines under oxidant- and ligand-free conditions. Notably, this catalytic system can also be applied to the direct and site-selective arylation of tetrahydroquinolines (C-8) and carbazoles (C-1).
Topics & Concepts
CatalysisArylChemistryLigand (biochemistry)PalladiumPyrimidineCombinatorial chemistryReaction conditionsOrganic chemistryStereochemistryReceptorAlkylBiochemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsRadical Photochemical Reactions