Heterogeneous Pd/C-catalyzed ligand-free, room-temperature Suzuki-Miyaura coupling reactions in aqueous media.
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.
Maegawa
Tomohiro
T
Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, Mitahora-higashi, Gifu 502-8585, Japan.
Kitamura
Yoshiaki
Y
Sako
Satoko
S
Udzu
Takahiro
T
Sakurai
Ai
A
Tanaka
Asami
A
Kobayashi
Yusuke
Y
Endo
Koichi
K
Bora
Utpal
U
Kurita
Takanori
T
Kozaki
Atsushi
A
Monguchi
Yasunari
Y
Sajiki
Hironao
H
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
D001897:Boronic Acids; D006846:Hydrocarbons, Halogenated; D008024:Ligands; D012997:Solvents; D014753:Vinyl Compounds; D014867:Water; D010165:Palladium; D002244:Carbon; D008697:Methane