A Convenient Photocatalytic Fluorination of Unactivated CH Bonds

Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site-selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination...

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Bibliographic Details
Published in:Angewandte Chemie 2014-04, Vol.126 (18), p.4778
Main Authors: Halperin, Shira D, Fan, Hope, Chang, Stanley, Martin, Rainer E, Britton, Robert
Format: Article
Language:ger
Subjects:
Chemistry
Fluorides
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Summary:Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site-selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination of unactivated CH bonds remains a significant challenge. Reported herein is a convenient and economic process for direct fluorination of unactivated CH bonds that exploits the hydrogen abstracting ability of a decatungstate photocatalyst in combination with the mild fluorine atom transfer reagent N-fluorobenzenesulfonimide. This operationally straightforward reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acid derivatives. [PUBLICATION ABSTRACT]
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201400420