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Oxovanadium(V)-Catalyzed Deoxygenative Coupling Reaction of Alcohols with Trimethylsilyl Enol Ethers in the Presence of MS3A |
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| Authors: | Takanari Matsutani Dr. Takashi Sakuramoto Kento Okabayashi Prof. Mamoru Tobisu Prof. Toshiyuki Moriuchi |
| Affiliation: | 1. Division of Molecular Materials Science, Graduate School of Science, Osaka City University, 3-3-138 Sugimoto, Sumiyoshi-ku, 558-8585 Osaka, Japan Contribution: Data curation (equal), Investigation (equal);2. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, 565-0871 Osaka, Japan Contribution: Data curation (equal), Investigation (equal);3. Division of Molecular Materials Science, Graduate School of Science, Osaka City University, 3-3-138 Sugimoto, Sumiyoshi-ku, 558-8585 Osaka, Japan Contribution: Data curation (supporting), Investigation (supporting);4. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, 565-0871 Osaka, Japan;5. Division of Molecular Materials Science, Graduate School of Science, Osaka City University, 3-3-138 Sugimoto, Sumiyoshi-ku, 558-8585 Osaka, Japan |
| Abstract: | Oxovanadium(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. |
| Keywords: | allyl alcohol deoxygenative coupling homogeneous catalysis trimethylsilyl enol ethers vanadium |