title: Copper-facilitated Suzuki reactions: application to 2-heterocyclic boronates.
abstract: The palladium-catalyzed Suzuki-Miyaura reaction has been utilized as one of the most powerful methods for C-C bond formation. However, Suzuki reactions of electron-deficient 2-heterocyclic boronates generally give low conversions and remain challenging. The successful copper(I) facilitated Suzuki coupling of 2-heterocyclic boronates that is broad in scope is reported. Use of this methodology affords greatly enhanced yields of these notoriously difficult couplings. Furthermore, mechanistic investigations suggest a possible role of copper in the catalytic cycle.
authors.affiliation: Department of Medicinal Chemistry, Merck Research Laboratories, P.O. Box 4, West Point, Pennsylvania 19486, USA. james_deng@merck.com
authors.forename: James Z
authors.initials: JZ
authors.lastname: Deng
authors.forename: Daniel V
authors.initials: DV
authors.lastname: Paone
authors.forename: Anthony T
authors.initials: AT
authors.lastname: Ginnetti
authors.forename: Hideki
authors.initials: H
authors.lastname: Kurihara
authors.forename: Spencer D
authors.initials: SD
authors.lastname: Dreher
authors.forename: Steven A
authors.initials: SA
authors.lastname: Weissman
authors.forename: Shaun R
authors.initials: SR
authors.lastname: Stauffer
authors.forename: Christopher S
authors.initials: CS
authors.lastname: Burgey
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*
chemical_list: D001897:Boronic Acids; D006571:Heterocyclic Compounds; D003300:Copper