Synthesis of crowded triarylphosphines carrying functional sites

Shigeru Sasaki, Fumiki Murakami, Midori Murakami, Mariko Watanabe, Kiyotoshi Kato, Katsuhide Sutoh, Masaaki Yoshifuji

Research output: Contribution to journalConference articlepeer-review

27 Citations (Scopus)

Abstract

4,4′-Diphosphinobiaryls and 1,3- and 1,4-borylphosphinobenzenes carrying crowded triarylphosphine moieties were synthesized by reaction of the corresponding diarylchlorophosphine with an arylcopper(I) reagent. Intramolecular interaction of the phosphorus redox center with the other phosphorus or the boron redox center was investigated by cyclic voltammetry. 4,4′-Diphosphinobiaryls displayed two-step reversible redox waves with slight differences of the oxidation potentials due to weak interaction between two phosphorus redox centers across 4,4′-biarylene linkage. Borylphosphinobenzenes showed two step redox waves corresponding to oxidation at the phosphorus and reduction at the boron. Although significant interaction between the phosphorus and boron redox centers was not observed in the cyclic voltammograms due to large difference of the redox potentials between phosphorus and boron redox centers, an absorption due to weakly interacting phosphorus and boron was observed in the UV-Vis spectrum of the 1,4-borylphosphinobenzene.

Original languageEnglish
Pages (from-to)2664-2672
Number of pages9
JournalJournal of Organometallic Chemistry
Volume690
Issue number10
DOIs
Publication statusPublished - 2005 May 16
Event16th International Conference on Phosphorus Chemistry ICPC -
Duration: 2004 Jul 42004 Jul 9

Keywords

  • Biaryl
  • Cyclic voltammetry
  • Triarylborane
  • Triarylphosphine

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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