A Facile and Potent Synthesis of meso , meso ‐Linked Porphyrin Arrays Using Iodine( III ) Reagents

The synthesis of meso , meso ‐linked fluoroalkylporphyrin arrays has been accomplished, in excellent yields, by the simple treatment of a CHCl 3 solution of zincated 5‐fluoroalkyl‐10,20‐diarylporphyrins (where fluoroalkyl = CF 3 , ClC 2 F 4 , n ‐ClC 4 F 8 , n ‐C 6 F 13 , etc.) with iodine( III ) reagents such as PhI(O–CO–CF 3 ) 2 (PIFA, also named as bis(trifluoroacetoxy)iodo]benzene) or PhI(OAc) 2 (PIDA). For nonfluorinated zincated 5‐substituted‐10–20‐diarylporphyrins (where substituent = phenyl, 4‐methoxyphenyl, 4‐methylphenyl, etc.) the similar coupling reactions also proceed fast and quantitatively. Moreover, various 15‐unsubstituted metalloporphyrins can also be coupled in high yields. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)