Synthesis of trifluoromethyl-porphyrins and -chlorins

Abstract

Reaction of zinc 5,15-bis(3,5-di-tert-butylphenyl)porphyrin with S- (trifluoromethyl)-3,7-dinitrobenzothiophene trifluoromethanesulfonate in tetrahydrofuran gave the 10-trifluoromethylated compound as the major product and 2-CF3- and 10,20-di-CF3-porphyrins as the minor products. The direct trifluoromethylation is effective for preparation of longer-wavelength absorbing meso-trifluoromethylated porphyrins and chlorins.