Palladium-Catalyzed Amidation of Aryl Halides Using 2‑Dialkylphosphino-2′-alkoxyl-1,1′-binaphthyl as Ligands
journal contributionposted on 15.06.2012, 00:00 by Fangfang Ma, Xiaomin Xie, Lei Zhang, Zhiyong Peng, Lina Ding, Lei Fu, Zhaoguo Zhang
Palladium-catalyzed intermolecular C–N bond-forming reactions between aryl halides and amides are described using 2-dialkylphosphino-2′-alkoxyl-1,1′-binaphthyl, which is both bulky and electron-rich, as the ligand. A variety of amides, including aliphatic and aromatic primary amides, lactams, and carbamates, were viable substrates for the amidation, which exhibited good functional group compatibility. By tuning the substituents at the 2,2′-position of 1,1′-binaphthyl of the ligand, the palladium-catalyzed amidation of bulky aryl halides was realized and this coupling reaction was used to synthesize 2-amino-2′-methoxy-1,1′-binaphthyl in high yield.