title: Pd-catalyzed aryl amination mediated by well defined, N-heterocyclic carbene (NHC)-Pd precatalysts, PEPPSI.
abstract: Pd-N-heterocyclic carbene (NHC)-catalyzed Buchwald-Hartwig amination protocols mediated by Pd-PEPPSI precatalysts is described. These protocols provide access to a range of hindered and functionalized drug-like aryl amines in high yield with both electron-deficient and electron-rich aryl- and heteroaryl chlorides and bromides. Variations in solvent polarity, base and temperature are tolerated, enhancing the scope and utility of this protocol. A mechanistic rationalization for base strength (pKb) requirements is also provided.
authors.affiliation: Chemistry Department, York University, 4700 Keele Street, Toronto, M3J 1P3, Canada. organ@yorku.ca
authors.forename: Michael G
authors.initials: MG
authors.lastname: Organ
authors.forename: Mirvat
authors.initials: M
authors.lastname: Abdel-Hadi
authors.forename: Stephanie
authors.initials: S
authors.lastname: Avola
authors.forename: Igor
authors.initials: I
authors.lastname: Dubovyk
authors.forename: Niloufar
authors.initials: N
authors.lastname: Hadei
authors.forename: Eric Assen B
authors.initials: EA
authors.lastname: Kantchev
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: O'Brien
authors.forename: Mahmoud
authors.initials: M
authors.lastname: Sayah
authors.forename: Cory
authors.initials: C
authors.lastname: Valente
mesh_terms: D000586:Amination; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006838:Hydrocarbons / Q000737:chemistry; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry; D013696:Temperature
chemical_list: D006571:Heterocyclic Compounds; D006838:Hydrocarbons; D008024:Ligands; D010720:Phosphines; C030011:carbene; D010165:Palladium; D008697:Methane