Brønsted Acid‐Catalyzed Carbonyl‐Olefin Metathesis inside a Self‐Assembled Supramolecular Host,Angewandte Chemie International Edition

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Brønsted Acid‐Catalyzed Carbonyl‐Olefin Metathesis inside a Self‐Assembled Supramolecular Host
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-01-11 , DOI: 10.1002/anie.201712141
Lorenzo Catti ₁ , Konrad Tiefenbacher _{1,

2}

Affiliation

Carbonyl–olefin metathesis represents a powerful yet underdeveloped method for the formation of carbon–carbon bonds. So far, no Brønsted acid based method for the catalytic carbonyl–olefin metathesis has been described. Herein, a cocatalytic system based on a simple Brønsted acid (HCl) and a self‐assembled supramolecular host is presented. The developed system compares well with the current benchmark catalyst for carbonyl–olefin metathesis in terms of substrate scope and yield of isolated product. Control experiments provide strong evidence that the reaction proceeds inside the cavity of the supramolecular host. A mechanistic probe indicates that a stepwise reaction mechanism is likely.

中文翻译：

自组装超分子主体内部的Brønsted酸催化的羰基-烯烃复分解

羰基-烯烃复分解法是形成碳-碳键的一种有力但尚未开发的方法。到目前为止，还没有描述基于布朗斯台德酸的催化羰基-烯烃复分解的方法。本文提出了一种基于简单布朗斯台德酸（HCl）和自组装超分子主体的助催化体系。在底物范围和分离产物的收率方面，该开发的系统与目前用于羰基-烯烃复分解反应的基准催化剂相当。对照实验提供了强有力的证据，表明该反应在超分子宿主腔内进行。机械探针表明可能是逐步反应机制。

更新日期：2018-01-11

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