title: meso,β-Oligohaloporphyrins as Useful Synthetic Intermediates of Diphenylamine-Fused Porphyrin and meso-to-meso β-to-β Doubly Butadiyne-Bridged Diporphyrin.
abstract: The chlorination of β-halo or β,β-dihaloporphyrins with 2-chloro-1,3-bis(methoxycarbonyl)guanidine (Palau'Chlor) proceeded selectively at the neighboring unsubstituted meso position to afford meso,β-dihalo or meso,β,β-trihaloporphyrins. Such oligohaloporphyrins are useful platforms for constructing more-elaborate porphyrin-based extended π systems. For example, meso-chloro-β,β-diiodoporphyrin participated in an efficient single-step synthesis of a diphenylamine-fused porphyrin. In addition, meso-chloro-β-iodoporphyrin was transformed in stepwise fashion into an efficiently conjugated meso-to-meso,β-to-β doubly butadiyne-linked porphyrin dimer, a system which was previously difficult to access without such haloporphyrin precursors.
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan).
authors.forename: Norihito
authors.initials: N
authors.lastname: Fukui
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan). yori@kuchem.kyoto-u.ac.jp.|ACT-C, JST, Sakyo-ku, Kyoto 606-8502 (Japan). yori@kuchem.kyoto-u.ac.jp.
authors.forename: Hideki
authors.initials: H
authors.lastname: Yorimitsu
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan). osuka@kuchem.kyoto-u.ac.jp.
authors.forename: Atsuhiro
authors.initials: A
authors.lastname: Osuka
keywords: butadiyne bridge; fusion reaction; halogenation; porphyrinoids; π extension