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Synthesis 2021; 53(17): 2995-3000
DOI: 10.1055/a-1437-9917
special topic
Bond Activation – in Honor of Prof. Shinji Murai

Synthesis of Tetrasilatetrathia[8]circulenes through C–I and C–H Silylation

Shuhei Akahori
a   Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan
,
Tetsuaki Fujihara
b   Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan
,
Yasushi Tsuji
b   Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan
,
Hiroshi Shinokubo
a   Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan
,
Yoshihiro Miyake∗
a   Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan
› Author AffiliationsThis work was supported by a Grant-in-Aid for Scientific Research in the Innovative Area ‘Soft Crystals (No. 2903)’ (JSPS KAKENHI grant JP20H04668) and ‘Precisely Designed Catalysts with Customized Scaffolding (No. 2702)’ (JSPS KAKENHI grant 16H01013) from MEXT, Japan. S. A. expresses his gratitude for a JSPS Research Fellowship for Young Scientists (JP18J22906).
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Abstract

We have succeeded in the synthesis of various tetrasilatetrathia[8]circulenes with alkyl and aryl groups on the silicon atoms. We also disclosed the effect of phosphine ligands on palladium-catalyzed silylation of tetraiodotetrathienylene and rhodium-catalyzed intramolecular silylation of tetrasilyltetrathienylenes. Experimental and theoretical analysis revealed the effect of the substituents on the silicon atoms on their electronic property.

Key words

circulene - silole - bond activation - silylation - palladium - rhodium - phosphine ligand

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1437-9917.
  • Supporting Information


Publication History

Received: 05 March 2021

Accepted after revision: 15 March 2021

Accepted Manuscript online:
15 March 2021

Article published online:
07 April 2021

© 2021. Thieme. All rights reserved

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