New synthetic strategy for diporphyrins: Pinacol coupling-rearrangement

Sumito Tokuji, Chihiro Maeda, Hideki Yorimitsu, Atsuhiro Osuka

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A new peak for porphyrins! A new approach to methylene-bridged diporphyrins has been explored, which consists of SmI2-mediated pinacol coupling followed by BF3-assisted pinacol-to-pinacolone rearrangement (see scheme). Diporphyrin 1 can further undergo multiple, dehydrative C-C bond formation to yield tetrahydropentalene-fused porphyrin dimer 2 with a rigid gable structure.

Original languageEnglish
Pages (from-to)7154-7157
Number of pages4
JournalChemistry - A European Journal
Volume17
Issue number26
DOIs
Publication statusPublished - Jun 20 2011
Externally publishedYes

Keywords

  • acetylation
  • nickel
  • pinacol coupling-rearrangement
  • porphyrin
  • samarium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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