Palladium-Catalyzed Reduction of Acid Chlorides to Aldehydes with Hydrosilanes

Tetsuaki Fujihara; Cong Cong; Tomohiro Iwai; Jun Terao; Yasushi Tsuji

doi:10.1055/s-0032-1317155

Synlett, Table of Contents

Synlett 2012; 23(16): 2389-2392
DOI: 10.1055/s-0032-1317155

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Palladium-Catalyzed Reduction of Acid Chlorides to Aldehydes with Hydrosilanes

Tetsuaki Fujihara

Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan Fax: +81(75)3832514 Email: ytsuji@scl.kyoto-u.ac.jp

,

Cong Cong

Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan Fax: +81(75)3832514 Email: ytsuji@scl.kyoto-u.ac.jp

,

Tomohiro Iwai

Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan Fax: +81(75)3832514 Email: ytsuji@scl.kyoto-u.ac.jp

,

Jun Terao

Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan Fax: +81(75)3832514 Email: ytsuji@scl.kyoto-u.ac.jp

,

Yasushi Tsuji*

Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan Fax: +81(75)3832514 Email: ytsuji@scl.kyoto-u.ac.jp

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Abstract

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Abstract

An efficient synthesis of aldehydes from acid chlorides with hydrosilanes as a reducing agent in the presence of a palladium catalyst has been achieved. A simple mixture of commercially available Pd(dba)₂ and Mes₃P as a catalyst realized the reduction of various acid chlorides including aliphatic acid chlorides and α,β-unsaturated acid chlorides to the corresponding aldehydes in good to high yields under mild reaction conditions.

Key words

acid chloride - aldehyde - hydrosilane - palladium - phosphine

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References

References and Notes
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Supplementary Material

Supporting Information