Bronsted Acid-Catalyzed Carbonyl-Olefin Metathesis inside a Self-Assembled Supramolecular Host

被引：82
作者：
Catti, Lorenzo [1 ]
Tiefenbacher, Konrad [1 ,2 ]
机构：
[1] Univ Basel, Dept Chem, BPR 1096,POB 3350,Mattenstr 24a, CH-4002 Basel, Switzerland
[2] Swiss Fed Inst Technol, Dept Biosyst Sci & Engn, Mattenstr 26, CH-4058 Basel, Switzerland
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 44期
基金：
瑞士国家科学基金会; 欧洲研究理事会;
关键词：
host-guest systems; metathesis; self-assembly; supramolecular catalysis; pi interactions; RESORCINARENE CAPSULE; HEXAMERIC CAPSULES; SELECTIVITY; STABILITY; KETONES;
D O I：
10.1002/anie.201712141
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Carbonyl-olefin metathesis represents a powerful yet underdeveloped method for the formation of carbon-carbon bonds. So far, no Bronsted acid based method for the catalytic carbonyl-olefin metathesis has been described. Herein, a cocatalytic system based on a simple Bronsted 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.
引用
收藏
页码：14589 / 14592
页数：4
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