title: Metal-free fluorination of C(sp3)-H bonds using a catalytic N-oxyl radical.
abstract: A direct conversion of C(sp(3))-H bonds to C(sp(3))-F bonds has been developed. In this process, a catalytic N-oxyl radical generated from N,N-dihydroxypyromellitimide abstracts hydrogen from the C(sp(3))-H bond and Selectfluor acts to trap the resulting carbon radical to form the C(sp(3))-F bond. This simple metal-free protocol enables the chemoselective introduction of a fluorine atom into various aromatic and aliphatic compounds and serves as a powerful tool for the efficient synthesis of fluorinated molecules.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Yuuki
authors.initials: Y
authors.lastname: Amaoka
authors.forename: Masanori
authors.initials: M
authors.lastname: Nagatomo
authors.forename: Masayuki
authors.initials: M
authors.lastname: Inoue
mesh_terms: D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry*; D054879:Halogenation; D006860:Hydrogen Bonding; D008670:Metals / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D008670:Metals; D005461:Fluorine; D002244:Carbon