Iridium-Catalyzed Asymmetric Hydrogenation of Simple Ketones with Tridentate PNN Ligands Bearing Unsymmetrical Vicinal Diamines

An iridium catalytic system with a ferrocene-based phosphine ligand bearing a modular and tunable unsymmetrical vicinal diamine scaffold was developed for the asymmetric hydrogenation of aryl ketones. This approach provided a powerful tool for the enantioselective synthesis of diverse chiral alcohols with excellent reactivity and enantioselectivity (up to 99% yield, up to 99% ee, and up to 50,000 turnover number). The substituents and chirality of unsymmetrical diamines in ligands played an important role in the satisfactory results.

Automated summary

An iridium catalytic system using a ferrocene-based phosphine ligand with a modular and tunable unsymmetrical vicinal diamine scaffold was developed for the asymmetric hydrogenation of aryl ketones. This method provided a powerful tool for the enantioselective synthesis of diverse chiral alcohols, exhibiting excellent reactivity and enantioselectivity (yield up to 99%, ee up to 99%, and turnover number up to 50,000). The substituents and chirality of unsymmetrical diamines in the ligands played a crucial role in achieving satisfactory results.