d0 Metal-Catalyzed Alkyl-Alkyl Cross-Coupling Enabled by a Redox-Active Ligand

Alkyl-alkyl cross-coupling through well-defined mechanisms that allow for controlled oxidative addition, prevent beta-hydride elimination, and tolerate hindered electrophiles is still challenging. Described herein is a redox-active ligand-enabled alkyl-alkyl cross-coupling using a d(0) metal. This tris(amido) Sc-III complex as well as the oxidized variant have been thoroughly characterized (NMR, X-ray, EPR, CV, UV-vis, DFT). Insight into the likely radical nature of the mechanism is disclosed. Additionally, a substrate scope that includes functional groups incompatible with late-transition-metal catalysis and both coupling partners bearing beta-hydrogens is reported.

Automated summary

This study describes a redox-active ligand-enabled alkyl-alkyl cross-coupling method using a d(0) metal, which allows for controlled oxidative addition, prevents beta-hydride elimination, and tolerates hindered electrophiles.