Palladium-Catalyzed Highly Regioselective Buchwald-Hartwig Amination of 5-Substituted-1,2,3-triiodobenzene: Facile Synthesis of 2,3-Diiodinated N-Arylanilines as Potential Anti-Inflammatory Candidates

Abstract A facile synthesis of 2,3-diiodinated N-arylaniline derivatives via highly regioselective Buchwald-Hartwig amination of 5-substituted-1,2,3-triiodobenzene is described. Remarkably, the amination reactions proceeded exclusively at the terminal positions, the less sterically hindered and the most regioactive positions. The highest yields were isolated from electron-poor/neutral 1,2,3-triiodoarenes and electron-poor anilines. The optimized reaction conditions were found to be tolerant for a wide range of different functional groups. This report discloses the first and unprecedent method to make 2,3-diiodinated N-arylanilines that is efficient, general in scope, highly regioselective and truly remarkable precursors for other transformations.