title: A convenient photocatalytic fluorination of unactivated C-H bonds.
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.
authors.affiliation: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia (Canada).
authors.forename: Shira D
authors.initials: SD
authors.lastname: Halperin
authors.forename: Hope
authors.initials: H
authors.lastname: Fan
authors.forename: Stanley
authors.initials: S
authors.lastname: Chang
authors.forename: Rainer E
authors.initials: RE
authors.lastname: Martin
authors.forename: Robert
authors.initials: R
authors.lastname: Britton
mesh_terms: D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry*; D005462:Fluorine Radioisotopes / Q000737:chemistry*; D054879:Halogenation; D006859:Hydrogen / Q000737:chemistry*; D008027:Light; D049268:Positron-Emission Tomography; D013449:Sulfonamides / Q000737:chemistry*; D000096926:Benzenesulfonamides
chemical_list: D002244:Carbon; D005461:Fluorine; D005462:Fluorine Radioisotopes; D006859:Hydrogen; D013449:Sulfonamides; C523711:N-fluorobenzenesulfonimide; D000096926:Benzenesulfonamides
keywords: CH activation; amino acids; photochemistry; polyoxometalates; tungsten