Synthesis of Aryl\nAlkyl\nThioethers via a Copper-Catalyzed\nThree-Component Reaction with DABSO, Aryldiazonium Salts, and Alkyl\nBromides

We\ndeveloped a method for synthesizing aryl alkyl thioether compounds\nvia a three-component reaction involving aryldiazonium salts, 1,4-diazabicyclo[2.2.2]octane\nbis(sulfur dioxide), and alkyl bromides. Optimal yields were achieved\nwhen a copper catalyst was used in conjunction with zinc and tetrabutylammonium\nbromide in an acetonitrile solvent at 130 °C for 10 h. This methodology\ndemonstrates good functional group tolerance and enables the successful\nsynthesis of various aryl alkyl thioethers with moderate to high yields.