An Improvement of the Palladium-Catalyzed [4+2] Cycloaddition of o-(Silylmethyl)benzyl Carbonates with Alkenes

Yushu Jin; Kentaro Ishizuka; Ryoichi Kuwano

doi:10.1055/s-0034-1379014

Synlett, Table of Contents

Synlett 2014; 25(17): 2488-2492
DOI: 10.1055/s-0034-1379014

letter

An Improvement of the Palladium-Catalyzed [4+2] Cycloaddition of o-(Silylmethyl)benzyl Carbonates with Alkenes

Yushu Jin

^aDepartment of Chemistry, Graduate School of Sciences, and International Research Center for Molecular Systems (IRCMS), Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan

,

Kentaro Ishizuka

^bEducation Center for Global Leaders in Molecular Systems for Devices, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan

,

Ryoichi Kuwano*

^aDepartment of Chemistry, Graduate School of Sciences, and International Research Center for Molecular Systems (IRCMS), Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan

^cJST ACT-C, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan Fax: +81(92)6422572 Email: rkuwano@chem.kyushu-univ.jp

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Abstract

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Abstract

The palladium complex, which is generated in situ from Pd(η ³-C₃H₅)Cp and tris(4-methoxy-3,5-dimethylphenyl)phosphine, catalyzed the [4+2] cycloaddition of o-(silylmethyl)benzyl carbonates with alkenes. The reaction of the benzyl esters with methyl crotonate gave methyl 3-methyltetralin-2-carboxylate in 84% yield with 2% catalyst loading.

Key words

catalysis - cycloaddition - o-quinodimethanes - alkenes - palladacycles

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References

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