Fluorinated Biaryl N-Heterocyclic Carbene Ligand with Noncovalent Interaction for Cu-Catalyzed Diastereoselective Addition Reaction

Abstract

A new class of biaryl Imidazo[1,5-a]pyridin-3-ylidene (ImPy) ligands featuring a Cu─F interaction and a C5-aryl substituent were developed for the diastereoselective addition reactions of easily accessible 1,3-enyne to ketones. X-ray and noncovalent interaction (NCI) analysis indeed demonstrated the presence of a Cu─F interaction and a Cu-arene interaction in the F–ImPy–Cu catalyst. The F–ImPy–Cu complex is an effective catalyst for the diastereoselective addition of a 1,3-enyne nucleophile to ketones, showing up to 96% yields and up to >10:1 diastereoselectivities. © 2025 Wiley-VCH GmbH.