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可见光介导的N-O键氧化还原断裂引发的芳烃的自由基三氟甲氧基化反应

Radical Trifluoromethoxylation of Arenes Triggered by a Visible-Light-Mediated N-O Bond Redox Fragmentation.

作者信息

Jelier Benson J, Tripet Pascal F, Pietrasiak Ewa, Franzoni Ivan, Jeschke Gunnar, Togni Antonio

机构信息

Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, Vladimir-Prelog-Weg 2, 8093, Zürich, Switzerland.

Department of Chemistry, University of Toronto, Toronto, M5S 3H6, Canada.

出版信息

Angew Chem Int Ed Engl. 2018 Oct 15;57(42):13784-13789. doi: 10.1002/anie.201806296. Epub 2018 Aug 7.

Abstract

A simple trifluoromethoxylation method enables non-directed functionalization of C-H bonds on a range of substrates, providing access to aryl trifluoromethyl ethers. This light-driven process is distinctly different from conventional procedures and occurs through an OCF radical mechanism mediated by a photoredox catalyst, which triggers an N-O bond fragmentation. The pyridinium-based trifluoromethoxylation reagent is bench-stable and provides access to synthetic diversity in lead compounds in an operationally simple manner.

摘要

一种简单的三氟甲氧基化方法能够对一系列底物上的C-H键进行非定向官能化,从而获得芳基三氟甲基醚。这种光驱动过程与传统方法明显不同,它通过光氧化还原催化剂介导的OCF自由基机制发生,该机制会引发N-O键断裂。基于吡啶鎓的三氟甲氧基化试剂在室温下稳定,并且以操作简单的方式为先导化合物的合成多样性提供了途径。

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