A Convenient Photocatalytic Fluorination of Unactivated CH Bonds |
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Authors: | Shira D. Halperin Hope Fan Stanley Chang Dr. Rainer E. Martin Prof. Robert Britton |
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Affiliation: | 1. Department of Chemistry, Simon Fraser University, Burnaby, British Columbia (Canada);2. Medicinal Chemistry, Small Molecule Research, Pharma Research & Early Development (pRED), F. Hoffmann‐La Roche AG, Grenzacherstrasse 124, 4070 Basel (Switzerland) |
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Abstract: | 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 C? H bonds remains a significant challenge. Reported herein is a convenient and economic process for direct fluorination of unactivated C? H 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. |
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Keywords: | amino acids C H activation photochemistry polyoxometalates tungsten |
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