Yang Han, Sun Xiaojie, Chen Zhen, Jiang Chenming, Duan Longhui, Zhao Jinbo, Gu Zhenhua
Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026, P. R. China.
Faculty of Chemistry and Biology, Changchun University of Technology, 2055 Yan'An Street, Changchun, Jilin, 130012, P. R. China.
Angew Chem Int Ed Engl. 2025 Jan 21;64(4):e202416839. doi: 10.1002/anie.202416839. Epub 2024 Nov 7.
Bipyridines represent a class of ligands renowned for their versatility and efficacy in numerous transition metal-catalyzed reactions. Chiral bipyridine ligands are noted for their distinctive reactivity and stereoselectivity. In this work, we have designed and synthesized a class of bipyridine ligands endowed with an axially chiral scaffold. These ligands feature: (a) a precisely aligned coplanar bipyridine framework that is beneficial for metal chelation; (b) a spacious environment around the metal-bipyridine complexes, capable of hosting substrates with substantial steric bulk; (c) a chiral pocket induced by the axially chiral architecture. These atropochiral planar bipyridine ligands were successfully applied in copper-catalyzed ring-opening reactions of cyclic diaryliodoniums with bulky secondary amines, achieving high efficiency and stereoselectivity that were unsuccessful in our previous efforts.
