Monodentate Chiral N-Heterocyclic Carbene–Palladium-Catalyzed Asymmetric Suzuki–Miyaura and Kumada Coupling

Abstract

N-Heterocyclic carbene ligands derived from C ₂-symmetric diamine with naphthyl side chains are introduced as chiral monodentate ligands, and their palladium complexes (NHC)Pd(cin)Cl are prepared. These compounds exist as a mixture of diastereomers, and the palladium complexes can be successfully separated. When used in the asymmetric Suzuki–Miyaura and ­Kumada coupling, chiral biaryls can be obtained in high yield and moderate selectivity.

Key words

monodentate chiral NHC - palladium - asymmetric ­catalysis - Suzuki–Miyaura coupling - Kumada coupling

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