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Two-Step, One-Flask Synthesis of an N-Confused Porphyrin Bearing Pentafluorophenyl Substituents
Julia M Fisher1, Victoria K Kensy1, G Richard Geier1
1Colgate University , Department of Chemistry, 13 Oak Drive, Hamilton, New York 13346, United States.
Abstract:
A two-step, one-flask reaction of pyrrole and pentafluorobenzaldehyde was investigated as a streamlined synthetic route to an N-confused porphyrin bearing pentafluorophenyl substituents previously prepared by a stepwise route. A survey of acid catalysts, acid catalyst concentration, DDQ quantity, and reaction time was performed with monitoring by HPLC. The targeted N-confused porphyrin was observed from many reaction conditions. The best condition afforded the N-confused porphyrin in an isolated yield of 10-12% (245-281 mg), providing improved access to this interesting porphyrinoid.