A Stereoselective Approach to (Z)-1-Silyl-2-aryl-1,3-dienes from 4-(Phenylselanyl)but-1-yne via Palladium-Catalyzed Silylstannylation and Selenoxide Elimination

Kazuki Shintaku; Hajime Maeda; Masahito Segi

doi:10.1055/s-0032-1317946

Synthesis, Table of Contents

Synthesis 2013; 45(3): 341-346
DOI: 10.1055/s-0032-1317946

paper

A Stereoselective Approach to (Z)-1-Silyl-2-aryl-1,3-dienes from 4-(Phenylselanyl)but-1-yne via Palladium-Catalyzed Silylstannylation and Selenoxide Elimination

Kazuki Shintaku

Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa 920-1192, Japan Fax: +81(76)2344800 Email: segi@se.kanazawa-u.ac.jp

,

Hajime Maeda

Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa 920-1192, Japan Fax: +81(76)2344800 Email: segi@se.kanazawa-u.ac.jp

,

Masahito Segi*

Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa 920-1192, Japan Fax: +81(76)2344800 Email: segi@se.kanazawa-u.ac.jp

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Abstract

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Abstract

The palladium-catalyzed silylstannylation of 4-(phenylselanyl)but-1-yne proceeded regio- and stereoselectively, followed by selenoxide elimination via oxidation to give (Z)-1-(trimethylsilyl)-2-(tributylstannyl)buta-1,3-diene in good yield. This conjugated diene underwent the Stille coupling reaction with various aryl iodides in the presence of Pd(PPh₃)₄ to afford (Z)-2-aryl-1-(trimethylsilyl)buta-1,3-dienes with high stereoselectivity. Reversing the order of selenoxide elimination and Stille coupling reaction in the synthetic procedure also resulted in good yields of (Z)-2-aryl-1-(trimethylsilyl)buta-1,3-dienes.

Key words

silylstannylation - selenide - Stille coupling reaction - selenoxide elimination - conjugated dienes - stereoselectivity

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References

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