Design and Synthesis of Tunable Chiral 2,2′-Bipyridine Ligands: Application to the Enantioselective Nickel-Catalyzed Reductive Arylation of Aldehydes

A new class of chiral 2,2'-bipyridine ligands, SBpy, featuring minimized short-range steric hindrance and structural tunability was rationally designed and developed, and the effectiveness was demonstrated in the first highly enantioselective Ni-catalyzed addition of aryl halides to aldehydes. In comparison with known approaches using preformed aryl metallic reagents, this reaction is more step-economical and functional group tolerant. The reaction mechanism and a model of stereocontrol were proposed based on experimental and computational results.

Automated summary

A new class of chiral bipyridine ligands, SBpy, featuring minimized steric hindrance and structural tunability, was designed and developed for the highly enantioselective Ni-catalyzed addition reaction. Compared to known methods, this reaction is more cost-effective and tolerant towards functional groups. The proposed reaction mechanism and stereocontrol model were based on experimental and computational results.