Green and fast 2-aryloxylation/amination of quinolines

A rapid, efficient and eco-friendly synthesis of 2-aroxyquinolines and 2-aminoquinolines was developed respectively through activating agent-promoted deoxygenative aryloxylation/amination. The main challenges in constructing C2-O or C2-N bonds from N-oxides lie in overcoming two side reactions: the reaction between the activating agent and the nucleophile, and the associated reaction at the C4-position. Compared to previous reports, this method benefits from an eco-friendly solvent, short reaction time, simple operation, and wide substrate scope, providing a variety of heteroaryl ethers and amines. We have demonstrated a gram-scale synthesis and calculated the green chemistry metrics to highlight the advantage of the developed synthetic method. The direct C2-H functionalization of quinolines has always been a widely concerned area. Herein we report a rapid and eco-friendly synthesis of 2-aroxyquinolines and 2-aminoquinolines through deoxygenative functionalization of quinoline N-oxides.