Unusual Fluoroalkenylation of Porphyrins: A Highly Stereoselective Synthesis of 10,20-Diaryl-5-[(E)-fluoroalkenyl]-15-(fluoroalkyl)porphyrins

A series of 10,20-diaryl-5-[(E)-fluoroalkenyl]-15-(fluoroalkyl)porphyrins has been synthesized by the reaction of free-base 5,15-diarylporphyrins with fluoroalkyl iodides in the presence of Na2S2O4. Subsequent intramolecular cyclization of the corresponding (fluoroalkenyl)porphyrins occurs smoothly in refluxing toluene/H2O. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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