Fluoroalkylation of porphyrins: Preparation and characterization of meso- and β-fluoroalkyl-5,15-diarylporphyrins

Treatment of zinc(II) 5,15-diphenylporphyrin or free-base 5,15-diphenylporphyrin with 1.1 eq. of fluoroalkyl iodides (RfI) in the presence of 1.1 eq. Na2S2O4 in a mixture solvent of DMSO/THF at 45 °C for 1–2 h gave 2-fluoroalkyl-5,15-diphenylporphyrin and 5-fluoroalkyl-10,20-diphenylporphyrin in a ratio from 1/3 to 1/8 in almost 50% total yields. The 5-fluoroalkyl-10,20-diphenylporphyrins were further fluoroalkylated to yield bis-fluoroalkylporphyrins.