Palladium-catalyzed highly regioselective Buchwald-Hartwig amination of 5-substitute d-1,2,3-triiodob enzene: Facile synthesis of 2,3-diiodinated N -arylanilines as potential anti-inflammatory candidates

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 pro-ceeded exclusively at the terminal positions, the less sterically hindered and the most regioactive po-sitions. 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 differ-ent 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. (c) 2021 Elsevier B.V. All rights reserved.