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

J Org Chem. 2023 Aug 4;88(15):11056-11068. doi: 10.1021/acs.joc.3c01022. Epub 2023 Jul 18.

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).