Perfluoroalkylation of Triarylamines by EDA Complexes and Ulterior Sensitized [6π]‐Electrocyclization to Perfluoroalkylated Endo‐Carbazoles. Mechanistic and Photophysical Studies

Abstract

AbstractBlue LEDs‐irradiation of a mixture of N,N,N',N'‐tetramethylethylenediamine (TMEDA) and perfluoroalkyl iodides (RF−I) – Electron Donor Acceptor (EDA)‐complex – in the presence of triphenylamines (TPAs) in an aqueous solvent mixture afforded mono‐perfluoroalkylated triphenylamines (RF−TPA) in good yields. These RF−TPA were further subjected to acetone‐sensitized [6π]‐electrocyclization at 315 nm‐irradiation affording exclusively perfluoroalkylated endo‐carbazole derivatives (RF−CBz) in quantitative yields. Mechanistic studies and photophysical properties of products are studied.