Catalytic Ligand for Room-Temperature Ullmann-Type Coupling Reaction

Catalytic Ligand for Room-Temperature Ullmann-Type Coupling Reaction

N-([Biphenyl]-2-yl)-N'-(2-phenyl-1-naphthyl)-1,2-benzenediamine [B6606] serves as a catalytic ligand for copper(I) iodide (CuI) in Ullmann-type coupling reactions. Its key advantage is that the reaction can proceed at room temperature. As an example, the coupling of 3-bromoquinoline [B1013] with 1-(4-chlorobenzhydryl)piperazine [C1611] was carried out using sodium methoxide [S0485] in DMSO for 22 hours at room temperature under a nitrogen atmosphere. After purification by silica gel column chromatography, the product 3-[4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl]quinoline was obtained as a light yellow solid in 82% yield. The reaction was monitored by NMR.

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