title: Selective Monoarylation of Primary Amines Using the Pd-PEPPSI-IPent(Cl) Precatalyst.
abstract: A single set of reaction conditions for the palladium-catalyzed amination of a wide variety of (hetero)aryl halides using primary alkyl amines has been developed. By combining the exceptionally high reactivity of the Pd-PEPPSI-IPent(Cl) catalyst (PEPPSI=pyridine enhanced precatalyst preparation, stabilization, and initiation) with the soluble and nonaggressive sodium salt of BHT (BHT=2,6-di-tert-butyl-hydroxytoluene), both six- and five-membered (hetero)aryl halides undergo efficient and selective amination.
authors.affiliation: Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M3J1P3 (Canada).
authors.forename: Sepideh
authors.initials: S
authors.lastname: Sharif
authors.affiliation: Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M3J1P3 (Canada).
authors.forename: Richard P
authors.initials: RP
authors.lastname: Rucker
authors.affiliation: Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M3J1P3 (Canada).
authors.forename: Nalin
authors.initials: N
authors.lastname: Chandrasoma
authors.affiliation: Lilly Research Laboratories, A Division of Eli Lilly and Company, Indianapolis, IN 46285 (USA).
authors.forename: David
authors.initials: D
authors.lastname: Mitchell
authors.affiliation: Lilly Research Laboratories, A Division of Eli Lilly and Company, Indianapolis, IN 46285 (USA).
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Rodriguez
authors.affiliation: The Dow Chemical Company, Midland, MI 48674 (USA).
authors.forename: Robert D J
authors.initials: RD
authors.lastname: Froese
authors.affiliation: Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M3J1P3 (Canada). organ@yorku.ca.
authors.forename: Michael G
authors.initials: MG
authors.lastname: Organ
mesh_terms: D000586:Amination; D000588:Amines / Q000737:chemistry*; D002084:Butylated Hydroxytoluene / Q000031:analogs & derivatives / Q000737:chemistry; D002384:Catalysis; D006219:Halogens / Q000737:chemistry; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*
chemical_list: D000588:Amines; D006219:Halogens; D006841:Hydrocarbons, Aromatic; D011725:Pyridines; D002084:Butylated Hydroxytoluene; D010165:Palladium; C037667:3,5-di-tert-butyl-4-hydroxytoluene; C023666:pyridine
keywords: PEPPSI; amination; cross-coupling; palladium; selectivity