title: Highly efficient monophosphine-based catalyst for the palladium-catalyzed suzuki-miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters.
abstract: A highly active and efficient catalyst system derived from a palladium precatalyst and monophosphine ligands 1 or 2 for the Suzuki-Miyaura cross-coupling reaction of heteroaryl boronic acids and esters has been developed. This method allows for the preparation of a wide variety of heterobiaryls in good to excellent yields and displays a high level of activity for the coupling of heteroaryl chlorides as well as hindered aryl and heteroaryl halides. Specific factors that govern the efficacy of the transformation for certain heterocyclic motifs were also investigated.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
authors.forename: Kelvin
authors.initials: K
authors.lastname: Billingsley
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Buchwald
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry; D013876:Thiophenes / Q000737:chemistry
chemical_list: D001897:Boronic Acids; D004952:Esters; D005663:Furans; D006571:Heterocyclic Compounds; D006846:Hydrocarbons, Halogenated; D007211:Indoles; D010720:Phosphines; D011725:Pyridines; D011758:Pyrroles; D013876:Thiophenes; D010165:Palladium