Photoinduced Reaction of Diiodoperfluoroalkanes with Aromatic Compounds: Divergent Synthesis of Two Product Types

Abstract

Both UV-light-promoted and organic-dye-catalyzed visible light-promoted reactions of diiodoperfluoroalkanes with an iodine substituent at both ends and substituted anilines are attempted. In the reactions with 1,6- and 1,8-diiodoperfluoroalkanes in the presence of an excess amount of aniline, both ends of the iodide reacts to give a diamine, and the reaction with an excess amount of diiodide gives a monoiodide, in which one end of the diiodide has reacted with the aniline. In contrast, in the case of the 1,4-diiodoperfluoroalkane, the UV reaction yields cyclization products in which both ends of the diiodine has reacted with the same aromatic ring, while the visible light reaction yields products in which only one end has reacted. Since synthetic examples of such cyclization products are limited, the reaction with various aromatic compounds is tried and it has been shown that it is effective for electron-rich aromatic rings. The mechanism of these reactions is discussed and the importance of the redox potential of the iodides is pointed out.