title: Highly selective palladium-catalyzed cross-coupling of secondary alkylzinc reagents with heteroaryl halides.
abstract: The highly selective palladium-catalyzed Negishi coupling of secondary alkylzinc reagents with heteroaryl halides is described. The development of a series of biarylphosphine ligands has led to the identification of an improved catalyst for the coupling of electron-deficient heterocyclic substrates. Preparation and characterization of oxidative addition complex (L)(Ar)PdBr provided insight into the unique reactivity of catalysts based on CPhos-type ligands in facilitating challenging reductive elimination processes.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
authors.forename: Yang
authors.initials: Y
authors.lastname: Yang
authors.forename: Katrin
authors.initials: K
authors.lastname: Niedermann
authors.forename: Chong
authors.initials: C
authors.lastname: Han
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Buchwald
mesh_terms: D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007202:Indicators and Reagents; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*
chemical_list: D006846:Hydrocarbons, Halogenated; D007202:Indicators and Reagents; D008024:Ligands; D010720:Phosphines; D010165:Palladium