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 were 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 reacted to give a diamine, and the reaction with an excess amount of diiodide gave a monoiodide, in which one end of the diiodide had reacted with the aniline. In contrast, in the case of the 1,4-diiodoperfluoroalkane, the UV reaction yielded cyclization products in which both ends of the diiodine had reacted with the same aromatic ring, while the visible-light reaction yielded products in which only one end had reacted. Since synthetic examples of such cyclization products are limited, we tried the reaction with various aromatic compounds and showed that it is effective for electron-rich aromatic rings. We also discuss the mechanism of these reactions and point out the importance of the redox potential of the iodides.