布朗斯特酸催化下邻羟基苯乙烯与吲哚的反应——1,1-二芳基乙烷类化合物的合成

发布时间：2018-07-07 09:31

本文选题：布朗斯特酸催化 + 有机小分子催化　；参考：《有机化学》2016年05期

【摘要】：1,1-二芳基乙烷骨架存在于许多具有生物活性的分子中,该类化合物的合成受到了化学工作者的广泛关注.实现了在消旋磷酸催化下结构普通的邻羟基苯乙烯与吲哚的反应,高效高产率地合成了一系列具有结构多样性的1,1-二芳基乙烷类化合物(产率高达99%).该反应是基于邻羟基苯乙烯在消旋磷酸催化下异构化成邻亚甲基苯醌中间体,通过消旋磷酸对该中间体和吲哚的双氢键活化模式,实现该反应的高效性.该反应条件温和,底物适用性广,不仅为解决金属催化带来的金属残留、反应条件苛刻等问题提供了有效的策略,同时也拓展了利用有机小分子催化来合成1,1-二芳基乙烷类化合物的反应适用范围.
[Abstract]:The cytoskeleton of 1-diarylethane exists in many bioactive molecules, and the synthesis of this kind of compounds has been widely concerned by chemists. Under the catalysis of racemic phosphoric acid, a series of 1-diaryl ethane compounds with structural diversity (yield as high as 99%) were synthesized in high yield and high yield. This reaction is based on the isomerization of o-hydroxystyrene in the presence of racemic phosphoric acid to produce an intermediate of o-methylene benzoquinone. The high efficiency of the reaction is achieved by the activation mode of double hydrogen bond between the intermediate and indole by racemic phosphoric acid. The reaction conditions are mild and the substrate is widely applicable, which not only provides an effective strategy for solving the problems of metal residue caused by metal catalysis, but also harsh reaction conditions, etc. At the same time, the application of organic small molecule catalysis to the synthesis of 1 ~ (-1) -diaryl ethane compounds was also expanded.
【作者单位】：江苏师范大学化学化工学院;
【基金】：国家自然科学基金(No.21372002) 江苏高校品牌专业建设工程资助项目~~
【分类号】：O621.251

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