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 CHCL3 solution of zincated 5-fluoroalkyl10,20-diarylporphyrins (where fluoroalkyl = CF3, ClC2F4, n=ClC4F8, n-C6F13, etc.) with iodine(III) reagents such as PhI(OCO-CF3)(2) (PIFA, also named as bis(trifluoroacetoxy)iodolbenzene) 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. (c) Wiley-WCH Verlagh GmbH & Co, KGaA, 69451 Weinheim, Germany, 2005.