meso,β-Oligohaloporphyrins as Useful Synthetic Intermediates of Diphenylamine-Fused Porphyrin and meso-to-meso β-to-β Doubly Butadiyne-Bridged Diporphyrin†
Norihito Fukui
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Hideki Yorimitsu
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan)
ACT-C, JST, Sakyo-ku, Kyoto 606-8502 (Japan)
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan)Search for more papers by this authorCorresponding Author
Prof. Dr. Atsuhiro Osuka
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan)
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan)Search for more papers by this authorNorihito Fukui
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Hideki Yorimitsu
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan)
ACT-C, JST, Sakyo-ku, Kyoto 606-8502 (Japan)
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan)Search for more papers by this authorCorresponding Author
Prof. Dr. Atsuhiro Osuka
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan)
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan)Search for more papers by this authorThis work was supported by Grants-in-Aid from MEXT (Nos.: 25107002 “Science of Atomic Layers”) and from JSPS (Nos.: 25220802 (Scientific Research (S)), 24685007 (Young Scientists (A)), 26620081 (Exploratory Research)).
Graphical Abstract
Doubled over: Chlorination of β-haloporphyrins with 2-chloro-1,3-bis(methoxycarbonyl)guanidine (Palau'Chlor) proceeded selectively at the neighboring unsubstituted meso position to afford meso,β-oligohaloporphyrins, which are useful intermediates of porphyrin-based extended π systems. For example, meso-chloro-β-iodoporphyrin was transformed stepwise into an efficiently conjugated meso-to-meso,β-to-β doubly butadiyne-linked porphyrin dimer.
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.
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