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三氟甲磺酸过渡金属催化醇、醚和酯转化为烯烃。

Transition metal triflate catalyzed conversion of alcohols, ethers and esters to olefins.

作者信息

Keskiväli J, Parviainen A, Lagerblom K, Repo T

机构信息

Department of Chemistry, University of Helsinki A. I. Virtasen aukio 1, P.O. Box 55 00014 Finland

出版信息

RSC Adv. 2018 Apr 23;8(27):15111-15118. doi: 10.1039/c8ra02437e. eCollection 2018 Apr 18.

Abstract

Herein, we report an efficient transition metal triflate catalyzed approach to convert biomass-based compounds, such as monoterpene alcohols, sugar alcohols, octyl acetate and tea tree oil, to their corresponding olefins in high yields. The reaction proceeds through C-O bond cleavage under solvent-free conditions, where the catalytic activity is determined by the oxophilicity and the Lewis acidity of the metal catalyst. In addition, we demonstrate how the oxygen containing functionality affects the formation of the olefins. Furthermore, the robustness of the used metal triflate catalysts, Fe(OTf) and Hf(OTf), is highlighted by their ability to convert an over 2400-fold excess of 2-octanol to octenes in high isolated yields.

摘要

在此,我们报道了一种高效的三氟甲磺酸过渡金属催化方法,可将基于生物质的化合物,如单萜醇、糖醇、乙酸辛酯和茶树油,高产率地转化为相应的烯烃。该反应在无溶剂条件下通过C-O键断裂进行,其中催化活性由金属催化剂的亲氧性和路易斯酸度决定。此外,我们展示了含氧化官能团如何影响烯烃的形成。此外,所使用的三氟甲磺酸金属催化剂Fe(OTf)₃和Hf(OTf)₄的稳健性体现在它们能够以高分离产率将超过2400倍过量的2-辛醇转化为辛烯。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ffd/9080037/707bbfce958f/c8ra02437e-f1.jpg

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