Aryl triolborates: novel reagent for copper-catalyzed N arylation of amines, anilines, and imidazoles.
The N arylation of primary and secondary aliphatic amines, anilines, and imidazoles with novel potassium aryl triolborates was carried out in the presence of a reoxidant and a catalytic amount of Cu(OAc)(2) (10 mol %). Aryl triolborates were found to be better reagents than aryl boronic acids or potassium aryl trifluoroborates as the former achieved high yields under mild conditions. Coupling of primary and secondary aliphatic amines to give N-aryl amines in excellent yields was performed under oxygen atmosphere. The reactions of anilines and imidazoles to provide N-aryl anilines and N-aryl imidazoles in good yields proceeded smoothly when trimethylamine N-oxide was used as an oxidant.
Yu
Xiao-Qiang
XQ
Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, N13W8, Sapporo 060-8628, Japan.
Yamamoto
Yasunori
Y
Miyaura
Norio
N
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D010880:Piperidines / Q000737:chemistry
D000588:Amines; D000814:Aniline Compounds; D001881:Borates; D007093:Imidazoles; D010880:Piperidines; C032727:piperidine; D003300:Copper; D006859:Hydrogen; D009584:Nitrogen; C023650:aniline