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

Shuhei Akahori; Tetsuaki Fujihara; Yasushi Tsuji; Hiroshi Shinokubo; Yoshihiro Miyake

doi:10.1055/a-1437-9917

Synthesis, Table of Contents

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

^aDepartment of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan

,

Tetsuaki Fujihara

^bDepartment of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan

,

Yasushi Tsuji

^bDepartment of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan

,

Hiroshi Shinokubo

^aDepartment of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan

,

Yoshihiro Miyake∗

^aDepartment of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan

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Abstract

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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

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References

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