Photo-induced electron-transfer reaction of aryl perfluoroalkanesulfonates with anilines

Article abstract of DOI:10.1016/0022-1139(93)02901-P

Irradiation of mixtures of aryl perfluoroalkanesulfonates (R_fSO3C6H4X-p, X = H, Cl and Me) (1) and aniline (2a), N,N-dimethylaniline (2b) or N,N-diethylaniline (2c) results in the formation of 2-coupling products 3 and 4-coupling products 4.However, in the reactions of 2b and 2c, in addition to 3 and 4, arenes 5 and N-methylaniline (6a) or N-ethylaniline (6b) are also detected.The presence of p-dinitrobenzene, Bu^t2NO and hydroquinone suppresses the reaction significantly.A photo-induced electron-transfer mechanism is proposed.