A reusable polymer supported copper catalyst for the C–N and C–O bond cross-coupling reaction of aryl halides as well as arylboronic acids

A simple and industrially viable protocol for C–N and C–O coupling was reported here. The polymer supported heterogeneous copper catalyst was prepared from chloromethyl polystyrene using a simple procedure. O-Arylation of substituted phenols with various aryl halides was achieved using this copper catalyst in DMSO medium. This heterogeneous copper catalyst, also efficiently works for the N-arylation of N–H heterocycles with aryboronic acids in methanol. This catalyst was also effective in amination reaction of primary amines with aryl halides as well as arylboronic acids in DMSO medium. The effects of solvent, base and temperature for the O-Arylation and amination reactions were reported. Further, the catalyst can be easily recovered quantitatively by simple filtration and reused up to several times without sufficient loss of its catalytic activity.

Graphical abstractCopper complex was synthesized from macroporous chloromethylated polystyrene beads. The immobilized copper catalyst shows excellent catalytic activity in O-arylation of phenols with various aryl halides, N-arylation of N–H heterocycles with arylboronic acids and amination reactions of primary amines with aryl halides as well as arylboronic acids.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Copper complex was synthesized from macroporous chloromethylated polystyrene. ► This catalyst shows excellent catalytic activity in O-arylation reaction. ► This catalyst shows excellent catalytic activity in N-arylation reaction. ► This catalyst shows excellent catalytic activity in amination reactions.