Oxovanadium(V)‐Catalyzed Deoxygenative Coupling Reaction of Alcohols with Trimethylsilyl Enol Ethers in the Presence of MS3A

Author:

Matsutani Takanari1,Sakuramoto Takashi2,Okabayashi Kento1,Tobisu Mamoru2ORCID,Moriuchi Toshiyuki13ORCID

Affiliation:

1. Division of Molecular Materials Science Graduate School of Science Osaka City University 3-3-138 Sugimoto, Sumiyoshi-ku 558-8585 Osaka Japan

2. Department of Applied Chemistry Graduate School of Engineering Osaka University Yamada-oka, Suita 565-0871 Osaka Japan

3. Present address: Department of Chemistry Graduate School of Science Osaka Metropolitan University 3-3-138 Sugimoto, Sumiyoshi-ku 558-8585 Osaka Japan

Abstract

AbstractOxovanadium(V)‐catalyzed deoxygenative coupling reaction of allyl alcohols with trimethylsilyl enol ethers was demonstrated to afford γ,δ‐unsaturated carbonyl compounds in one‐step. The catalytic deoxygenative coupling reaction of allyl alcohols proceeded smoothly with both aromatic and aliphatic trimethylsilyl enol ethers. This catalytic deoxygenative coupling system could be applied to the deoxygenative coupling reaction of benzyl alcohols with trimethylsilyl enol ethers, providing the corresponding carbonyl compounds. Furthermore, a gram‐scale catalytic synthesis of the γ,δ‐unsaturated carbonyl compound was successfully performed to validate the scalability of this catalytic deoxygenative coupling reaction.

Funder

Osaka University

Osaka City University

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

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