603-34-9

4181-20-8

The general procedure for the synthesis of tris(4-iodophenyl)amine was as follows: first, IPe2BF4 (5.3 g, 14.3 mmol) and triphenylamine (1 g, 4.1 mmol) were mixed in CH2Cl2 (60 mL) and cooled to 0 °C under nitrogen protection. Subsequently, trifluoromethanesulfonic acid (TfOH: 900 μL, 4.1 mmol) was added slowly and dropwise. The reaction mixture was stirred at room temperature under nitrogen atmosphere for 21 h until a reddish brown solution was formed. After completion of the reaction, saturated aqueous NaHCO3 and Na2S2O3 were added to the mixture and the aqueous layer was extracted with CH2Cl2. The organic layers were combined and washed sequentially with saturated NaHCO3 and NaCl solutions and then dried with Na2SO4. The dried organic phase was filtered and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (eluent: hexane/EtOAc = 5/1) to afford tris(4-iodophenyl)amine (2.507 g, 99% yield). The product was characterized by 1H NMR and 13C NMR: 1H NMR (CDCl3) δ 7.54 (d, J = 8.9 Hz, 6H), 6.81 (d, J = 8.9 Hz, 6H); 13C NMR (CDCl3) δ 146.5, 138.4, 126.0. The NMR data confirm that the resulting compound is tris(4-iodophenyl)amine.