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
a   Department of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan   amori@kobe-u.ac.jp
,
Yushin Shibuya
a   Department of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan   amori@kobe-u.ac.jp
,
Toyoko Suzuki
a   Department of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan   amori@kobe-u.ac.jp
,
a   Department of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan   amori@kobe-u.ac.jp
,
Masaki Horie
b   Department of Chemical Engineering, National Tsing Hua University, 101, Sec. 2, Kuang-Fu Road, Hsinchu 30013, Taiwan
,
Atsunori Mori
a   Department of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan   amori@kobe-u.ac.jp
c   Research Center for Membrane Science and Technology, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan
› Institutsangaben
This work was partly supported by Kakenhi B (JP19182273) by MEXT, Cooperative Research Program of ‘Network Joint Research Center for Materials and Devices’, and Kobe University for the promotion of international collaboration researches.


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.

Supporting Information



Publikationsverlauf

Eingereicht: 25. Dezember 2020

Angenommen nach Revision: 21. Januar 2021

Accepted Manuscript online:
21. Januar 2021

Artikel online veröffentlicht:
15. Februar 2021

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