title: Regioselective radical aminofluorination of styrenes.
abstract: The copper-catalyzed radical aminofluorination of styrenes with N-fluorobenzenesulfonimide (NFSI) is realized with high regioselectivity, thus affording aminofluorination products with regioselectivities opposite that of the palladium-catalyzed and noncatalyzed processes. Preliminary mechanistic studies suggested the reaction went through a radical pathway and was supported by DFT calculations. In these reactions, NFSI is utilized as both a radical nitrogen source and radical fluorine source, thus rendering it an attractive reagent.
authors.affiliation: Department of Chemistry, Northeast Normal University, Changchun, 130024 (China).
authors.forename: Hongwei
authors.initials: H
authors.lastname: Zhang
authors.forename: Yongcheng
authors.initials: Y
authors.lastname: Song
authors.forename: Jinbo
authors.initials: J
authors.lastname: Zhao
authors.forename: Jingping
authors.initials: J
authors.lastname: Zhang
authors.forename: Qian
authors.initials: Q
authors.lastname: Zhang
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry; D013816:Thermodynamics; D000096926:Benzenesulfonamides
chemical_list: D003300:Copper; D005461:Fluorine; D005609:Free Radicals; D010165:Palladium; D013343:Styrenes; D013449:Sulfonamides; C523711:N-fluorobenzenesulfonimide; D000096926:Benzenesulfonamides
keywords: density functional calculations; fluorine; radicals; regioselectivity; synthetic methods