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

Abstract

Blue 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.