One-Shot Deprotonative Metalation/Transmetalation/Polymerization of Halothiophenes Catalyzed by Nickel Complex for Polythiophene Synthesis

Sonoka Yamamoto; Yushin Shibuya; Toyoko Suzuki; Kentaro Okano; Masaki Horie; Atsunori Mori

doi:10.1055/a-1368-7072

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(17): 3081-3084
DOI: 10.1055/a-1368-7072

special topic

Bond Activation – in Honor of Prof. Shinji Murai

One-Shot Deprotonative Metalation/Transmetalation/Polymerization of Halothiophenes Catalyzed by Nickel Complex for Polythiophene Synthesis

Sonoka Yamamoto

^aDepartment of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan amori@kobe-u.ac.jp

,

Yushin Shibuya

^aDepartment of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan amori@kobe-u.ac.jp

,

Toyoko Suzuki

^aDepartment of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan amori@kobe-u.ac.jp

,

Kentaro Okano

^aDepartment of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan amori@kobe-u.ac.jp

,

Masaki Horie

^bDepartment of Chemical Engineering, National Tsing Hua University, 101, Sec. 2, Kuang-Fu Road, Hsinchu 30013, Taiwan

,

Atsunori Mori ∗

^aDepartment of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan amori@kobe-u.ac.jp

^cResearch Center for Membrane Science and Technology, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan

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Abstract

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Abstract

Effect of divalent metals was studied in the cross-coupling polymerization of thiophenes leading to head-to-tail-type poly-3-hexylthiophene. Deprotonation of the C–H bond at the 5-position of 2-halo-3-hexylthiophene by LDA followed by metal exchange was carried out in one pot and following addition of nickel catalyst underwent polymerization. One-shot reaction involving deprotonation/transmetalation/ cross coupling polymerization was also examined with manganese(II) chloride and nickel(II) catalyst.

Key words

deprotonative metalation - poly(3-hexylthiophene) - group II metals - nickel catalyst - one-shot reaction

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Referenzen

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Zusatzmaterial

Supporting Information