Triphenylsilane-fused Porphyrins

Kenichi Kato, Jun Oh Kim, Hideki Yorimitsu, Dongho Kim, Atsuhiro Osuka

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Abstract

A reaction sequence of 2-(diphenylsilyl)phenylation by Negishi coupling and intramolecular sila-Friedel–Crafts reaction has been explored for the synthesis of mono-triphenylsilane-fused porphyrins 5 M and 6 M (M= Ni, Zn) and bis-triphenylsilane-fused porphyrins 7 M and 8 Ni. A triply linked triphenylsilane-fused Ni II porphyrin, 13 Ni, was synthesized in a stepwise manner involving the above reaction sequence and a final Pd-catalyzed C−H activating arylative cyclization. The silicon atom in 13 Ni takes a distorted planarized structure with an almost perpendicular Si-phenyl group, causing an electronic effect due to effective σ*–π* interaction.

Original languageEnglish
Pages (from-to)1738-1746
Number of pages9
JournalChemistry - An Asian Journal
Volume11
Issue number11
DOIs
Publication statusPublished - 2016 Jun 6

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry

Cite this

Kato, K., Kim, J. O., Yorimitsu, H., Kim, D., & Osuka, A. (2016). Triphenylsilane-fused Porphyrins. Chemistry - An Asian Journal, 11(11), 1738-1746. https://doi.org/10.1002/asia.201600424