Brønsted Acid‐Catalyzed Carbonyl‐Olefin Metathesis inside a Self‐Assembled Supramolecular Host. Issue 44 (11th January 2018)

• Record Type: Journal Article
• Authors: Catti, Lorenzo; Tiefenbacher, Konrad
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 44(2018)
• Page Start: 14589
• Page End: 14592
• Publication Date: 2018-01-11
• Subjects: host–guest systems -- metathesis -- self-assembly -- supramolecular catalysis -- π interactions; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201712141
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : Metathesis inside a host : A supramolecular host was used to develop a general method for Brønsted acid‐catalyzed carbonyl–olefin metathesis. This system provides comparable yields to the current Lewis acid benchmark catalyst. A mechanistic study indicated stepwise oxetane formation for some of the employed substrates.