Alkyl-alkyl cross-coupling through well-defined mechanisms that allow for controlled oxidative addition, prevent β-hydride elimination, and tolerate hindered electrophiles is still challenging. Described herein is a redox-active ligand-enabled alkyl-alkyl cross-coupling using a d0 metal. This tris(amido) ScIII 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 β-hydrogens is reported.
Bibliographical noteFunding Information:
Financial support was provided by the University of Minnesota and the Petroleum Research Fund of the American Chemical Society (ACS PRF 62432-DNI1).
© 2022 American Chemical Society.
- alkyl-alkyl bonds
- redox-active ligands
- scandium catalysis