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Synthesis 2016; 48(15): 2438-2448
DOI: 10.1055/s-0035-1561418
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1,2′-Biazulenes by Palladium-Catalyzed Unusual Homocoupling Reaction of 1-Haloazulenes in the Presence of Ferrocene

Taku Shoji*
a   Department of Chemistry, Faculty School of Science, Shinshu University, Matsumoto 390-8621, Nagano, Japan   eMail: tshoji@shinshu-u.ac.jp
b   Department of Material Science, Graduate School of Science and Technology, Shinshu University, Matsumoto 390-8621, Nagano, Japan
,
Kanami Miyashita
a   Department of Chemistry, Faculty School of Science, Shinshu University, Matsumoto 390-8621, Nagano, Japan   eMail: tshoji@shinshu-u.ac.jp
,
Takanori Araki
a   Department of Chemistry, Faculty School of Science, Shinshu University, Matsumoto 390-8621, Nagano, Japan   eMail: tshoji@shinshu-u.ac.jp
,
Miwa Tanaka
a   Department of Chemistry, Faculty School of Science, Shinshu University, Matsumoto 390-8621, Nagano, Japan   eMail: tshoji@shinshu-u.ac.jp
,
Akifumi Maruyama
b   Department of Material Science, Graduate School of Science and Technology, Shinshu University, Matsumoto 390-8621, Nagano, Japan
,
Ryuta Sekiguchi
c   Graduate School of Science and Technology, Hirosaki University, Hirosaki 036-8561, Aomori, Japan
,
Shunji Ito
c   Graduate School of Science and Technology, Hirosaki University, Hirosaki 036-8561, Aomori, Japan
,
Tetsuo Okujima
d   Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Ehime, Japan
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Publikationsverlauf

Received: 26. Januar 2016

Accepted after revision: 22. Februar 2016

Publikationsdatum:
22. März 2016 (online)

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Abstract

The synthesis of 1,2′-biazulenes was established by palladium-catalyzed homocoupling reactions of the corresponding 1-haloazulenes in the presence of ferrocene. The optical properties of the novel 1,2′-biazulenes were investigated by UV/Vis spectroscopy and theoretical calculations. The redox behaviors of 1,2′-biazulenes were also examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV).

Key words

azulene - 1,2′-biazulene - homocoupling - UV/Vis spectrum - cyclic voltammetry

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561418.
  • Supporting Information
 

  • References

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