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烷氧基硅烷促进仲苄醇与脂肪醇的交叉醚化反应：不对称二烷基醚的合成

Alkoxyhydrosilane-facilitated cross-etherification reaction of secondary benzyl alcohol with aliphatic alcohol: synthesis of unsymmetrical dialkyl ethers.

作者信息

Hashimoto Toru, Matsunaga Yakumo, Okamura Yuki, Takao Sosuke, Hojo Makoto

机构信息

Department of Applied Chemistry, Faculty of Engineering Sanyo-Onoda City University Sanyo-Onoda Yamaguchi 756-0884 Japan

Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Technology Hachioji Tokyo 192-0982 Japan.

出版信息

RSC Adv. 2024 Oct 4;14(43):31467-31470. doi: 10.1039/d4ra05997b. eCollection 2024 Oct 1.

DOI:10.1039/d4ra05997b
PMID:39372053
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11450445/
Abstract

Alkoxyhydorosilane is found to be an effective mediator for the cross-etherification reaction between two distinct alcohols, namely, a secondary benzyl alcohol and an aliphatic alcohol, providing the unsymmetrical dialkyl ethers in good-to-high yields. The reaction is also successfully applied to the lignin model compound, which is an important renewable non-fossil organic carbon source. Initial mechanistic studies indicated that the carbocation derived from benzyl alcohol was formed under the present reaction conditions.

摘要

发现烷氧基氢硅烷是两种不同醇（即仲苄醇和脂肪醇）之间交叉醚化反应的有效介质，能以良好至高收率提供不对称二烷基醚。该反应也成功应用于木质素模型化合物，木质素是一种重要的可再生非化石有机碳源。初步机理研究表明，在当前反应条件下会形成源自苄醇的碳正离子。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d02/11450445/f9975d90cff9/d4ra05997b-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d02/11450445/ab839bb09820/d4ra05997b-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d02/11450445/49501cd62782/d4ra05997b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d02/11450445/1073c871aa24/d4ra05997b-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d02/11450445/176a85f8701e/d4ra05997b-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d02/11450445/f070e3b4a83d/d4ra05997b-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d02/11450445/f9975d90cff9/d4ra05997b-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d02/11450445/ab839bb09820/d4ra05997b-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d02/11450445/f070e3b4a83d/d4ra05997b-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d02/11450445/f9975d90cff9/d4ra05997b-s7.jpg

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