title: Heterogeneous Pd/C-catalyzed ligand-free, room-temperature Suzuki-Miyaura coupling reactions in aqueous media.
abstract: A mild and efficient ligand-free Suzuki-Miyaura coupling reaction catalyzed by heterogeneous Pd/C was developed. Aryl bromides and triflates undergo the cross-coupling with aryl boronic acids in excellent yields without the presence of any additives in aqueous media at room temperature. Aryl vinyl boronic acids are also applicable to this coupling reaction and provide the trans-stilbene derivatives in high yields. The application of wet-type Pd/C to the coupling reaction was achieved without any loss of activity under aerobic conditions, and the reuse of Pd/C is feasible for a fifth run without significant loss of activity. Inductively coupled plasma (ICP) mass-spectrometric analysis of the filtrate from the reaction mixture of 4-bromonitrobenzene with phenylboronic acid demonstrated that the palladium metal hardly leached into the solution within the limits of the detector (<1 ppm), thus suggesting that the present Suzuki-Miyaura reaction proceeded by heterogeneous catalysis.
authors: Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, Mitahora-higashi, Gifu 502-8585, Japan.
authors: Tomohiro
authors: T
authors: Maegawa
authors: Yoshiaki
authors: Y
authors: Kitamura
authors: Satoko
authors: S
authors: Sako
authors: Takahiro
authors: T
authors: Udzu
authors: Ai
authors: A
authors: Sakurai
authors: Asami
authors: A
authors: Tanaka
authors: Yusuke
authors: Y
authors: Kobayashi
authors: Koichi
authors: K
authors: Endo
authors: Utpal
authors: U
authors: Bora
authors: Takanori
authors: T
authors: Kurita
authors: Atsushi
authors: A
authors: Kozaki
authors: Yasunari
authors: Y
authors: Monguchi
authors: Hironao
authors: H
authors: Sajiki
mesh_terms: D001897:Boronic Acids / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013696:Temperature; D014753:Vinyl Compounds / Q000737:chemistry; D014867:Water / Q000737:chemistry
chemical_list: D001897:Boronic Acids; D006846:Hydrocarbons, Halogenated; D008024:Ligands; D012997:Solvents; D014753:Vinyl Compounds; D014867:Water; D010165:Palladium; D002244:Carbon; D008697:Methane