Preparation and Application of New P, N-Ligands for Palladium-Catalyzed C–N Bond Coupling Reaction

doi:10.3724/SP.J.1088.2011.10617

Abstract

Abstract: P,N-ligands (L1–L5) with cyclic secondary amine moieties linked to the benzene rings of triphenylphosphine were designed and synthesized for the palladium-catalyzed C–N bond coupling reactions. The structures of these new P,N-ligands were confirmed by ¹H NMR, ¹³C NMR, ³¹P NMR, infrared, high resolution mass spectroscopy, and X-ray single crystal diffraction. The desired C–N bond coupling products were obtained in good to excellent yields (up to 95%) when the reactions of aryl bromides with secondary amines were performed under the optimized reaction conditions (Pd₂(dba)₃, 1 mol%; L5, 6 mol%; NaO^tBu, 1.4 mmol; toluene, 2.5 ml; 100 ^oC).

Key words: P,N-ligand, palladium catalysis, C–N bond coupling, aryl bromide, secondary amine

DAI Yao, LIU He-Song, FENG Xiu-Juan, BAO Ming. Preparation and Application of New P, N-Ligands for Palladium-Catalyzed C–N Bond Coupling Reaction[J]. Chinese Journal of Catalysis, 2011, 32(10): 1617-1623.

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