Pd-Catalyzed C-7 Arylation of Indolines with Aryltriazenes under Mild Conditions

A palladium-catalyzeddirect C-H arylation of indolinesat C-7 position has been achieved at near-ambient temperature. Thereaction was carried out with aryltriazene as a stable aryl sourceand electron shuttle to sustainably release aryl radical insitu under the action of promoter, and pyrimidine as a detachabledirecting group for the synthesis of 7-arylindolines under oxidant-and ligand-free conditions. Notably, this catalytic system can alsobe applied to the direct and site-selective arylation of tetrahydroquinolines(C-8) and carbazoles (C-1).

Automated summary

A palladium-catalyzed direct C-H arylation of indolines at C-7 position has been achieved at near-ambient temperature. The reaction utilizes aryltriazene as a stable aryl source and electron shuttle, pyrimidine as a detachable directing group, and proceeds under oxidant- and ligand-free conditions. This catalytic system also allows for direct and site-selective arylation of tetrahydroquinolines (C-8) and carbazoles (C-1).