Substrate or Solvent‐Controlled Pd II ‐Catalyzed Regioselective Arylation of Quinolin‐4(1 H )‐ones Using Diaryliodonium Salts: Facile Access to Benzoxocine and Aaptamine Analogues

Regioselective C3, C5, and C8 arylation of quinolin‐4(1 H )‐ones have been accomplished either by substrate‐control or by tuning the reaction solvent. A variety of aryl(mesityl)iodonium triflates could smoothly deliver arylated products in good to excellent yields. Additionally, it offers great flexibility by arylating medicinally potent quinolone related heterocycles such as acridin‐9(10 H )‐one, and phenanthridin‐6(5 H )‐one under standard reaction conditions. This strategy was further extended with diphenyleneiodonium triflate to access oxacine fused quinolines. The post‐modifications of synthesized products enhance the further utility of this protocol in organic synthesis. To the best of our knowledge, this is the first report on C5 arylation of quinolin‐4(1 H )‐ones using iodine(III) reagents.