Simple amine/Pd(OAc)(2)-catalyzed suzuki coupling reactions of aryl bromides under mild aerobic conditions.
A new palladium catalyst (DAPCy) made from Pd(OAc)(2) and commercially available, inexpensive dicyclohexylamine has been developed for the Suzuki coupling reaction of aryl bromides with boronic acids to give the coupling products in good to high yields. The air-stable catalyst was characterized and well-defined by X-ray crystallography. A catalytic system involving DAPCy in dioxane demonstrates a temperature-dependent reactivity toward aryl bromides with different electronic substituents, and selectively couples electron-deficient aryl bromides with boronic acids over electron-rich ones at room temperature. Another catalytic system employing DAPCy in EtOH provides a general and convenient method to prepare biaryls from aryl bromides and boronic acids with a broad range of functional groups at room temperature and under aerobic conditions.
Tao
Bin
B
Department of Chemistry, MSC 8L0378, Georgia State University, 33 Gilmer Street, SE Unit 8, Atlanta, Georgia 30303-3088, USA.
Boykin
David W
DW
D000588:Amines / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis*; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis*; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
D000588:Amines; D001897:Boronic Acids; D006841:Hydrocarbons, Aromatic; D006842:Hydrocarbons, Brominated; D008024:Ligands; D010165:Palladium