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

Angew Chem Int Ed Engl. 2022 May 9;61(20):e202117843. doi: 10.1002/anie.202117843. Epub 2022 Feb 26.

Abstract

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.

Keywords: 2,2′-Bipyridine Ligands; Asymmetric Catalysis; Diaryl Carbinols; Enantioselectivity; Reductive Additions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2,2'-Dipyridyl
  • Aldehydes* / chemistry
  • Catalysis
  • Heterocyclic Compounds*
  • Ligands
  • Nickel / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Heterocyclic Compounds
  • Ligands
  • 2,2'-Dipyridyl
  • Nickel