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Ligand Relay Catalysis Enables Asymmetric Migratory Hydroarylation for the Concise Synthesis of Chiral α-(Hetero)Aryl-Substituted Amines.

Junqian ZhouYuli HeZihao LiuYou WangShaolin Zhu
Published in: Advanced science (Weinheim, Baden-Wurttemberg, Germany) (2024)
Complementary to the design of a single structurally complex chiral ligand to promote each step in transition-metal catalysis, multiligand relay catalysis through dynamic ligand exchange with each step in the catalytic cycle promoted by its best ligand provides an attractive approach to enhance the whole reaction reactivity and selectivity. Herein, a regio- and enantioselective NiH-catalyzed migratory hydroarylation process with a simple combination of a chain-walking ligand and an asymmetric arylation ligand, producing high-value chiral α-(hetero)aryl-substituted amines and their derivatives under mild conditions, is reported. The potential synthetic applications of this transformation are demonstrated by the concise synthesis of (S)-nicotine and a CDK8 inhibitor.
Keyphrases
  • ionic liquid
  • transition metal
  • molecular docking
  • capillary electrophoresis
  • cell cycle
  • room temperature
  • mass spectrometry
  • cell proliferation