title: Pd-catalyzed aryl C-H imidation with arene as the limiting reagent.
abstract: An amine-N-oxide-ligated palladium complex, in conjunction with a silver cocatalyst, catalyzes imidation of arenes by the reagent N-fluorobenzenesulfonimide. The reaction enables imidation of a variety of arenes at or below room temperature, requires no coordinating directing group on the substrate, and gives synthetically useful yields with only 1 equiv of arene. Mechanistic data implicate an unusual mechanism devoid of commonly invoked organometallic intermediates: oxidation of the Pd catalyst occurs as the turnover-limiting step, while C-H bond functionalization occurs subsequently at a high oxidation state of the catalyst.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138.
authors.forename: Gregory B
authors.initials: GB
authors.lastname: Boursalian
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138.
authors.forename: Ming-Yu
authors.initials: MY
authors.lastname: Ngai
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138.
authors.forename: Katarzyna N
authors.initials: KN
authors.lastname: Hojczyk
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138.
authors.forename: Tobias
authors.initials: T
authors.lastname: Ritter
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D007094:Imides / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D012834:Silver / Q000737:chemistry
chemical_list: D001555:Benzene Derivatives; D007094:Imides; D009942:Organometallic Compounds; D012834:Silver; D010165:Palladium