A Convenient Photocatalytic Fluorination of Unactivated CH Bonds

• Published in: Angewandte Chemie International Edition Vol. 53; no. 18; pp. 4690 - 4693
• Main Authors: Halperin, Shira D., Fan, Hope, Chang, Stanley, Martin, Rainer E., Britton, Robert
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 25.04.2014; WILEY‐VCH Verlag; Wiley
• Subjects: Amino acids; Blocking; Carbon - chemistry; Catalysis; Chemistry; Chemistry, Multidisciplinary; CH activation; Derivatives; Economics; Fluorides; Fluorination; Fluorine - chemistry; Fluorine Radioisotopes - chemistry; Halogenation; Hydrogen - chemistry; Light; Natural products; Photocatalysis; photochemistry; Physical Sciences; polyoxometalates; Positron-Emission Tomography; Science & Technology; Sulfonamides - chemistry; Tomography; tungsten; EXCITED-STATE; ACIDS; amino acids; REACTIVITY; ALDEHYDES; MEDICINAL CHEMISTRY; ALKENES; CH activation; tungsten; photochemistry; polyoxometalates; RADICALS; PET; ALKANES; CH activation
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.201400420

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 ing 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. The direct fluorination of unactivated C(sp3)H bonds is catalyzed by the inexpensive photocatalyst tetrabutylammonium decatungstate (TBADT). This convenient reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acids.