title: Two-Step, One-Flask Synthesis of an N-Confused Porphyrin Bearing Pentafluorophenyl Substituents.
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.
authors.affiliation: Colgate University , Department of Chemistry, 13 Oak Drive, Hamilton, New York 13346, United States.
authors.forename: Julia M
authors.initials: JM
authors.lastname: Fisher
authors.affiliation: Colgate University , Department of Chemistry, 13 Oak Drive, Hamilton, New York 13346, United States.
authors.forename: Victoria K
authors.initials: VK
authors.lastname: Kensy
authors.affiliation: Colgate University , Department of Chemistry, 13 Oak Drive, Hamilton, New York 13346, United States.
authors.forename: G Richard
authors.identifier: 0000-0001-9751-6190
authors.initials: GR
authors.lastname: Geier