D0Metal-Catalyzed Alkyl-Alkyl Cross-Coupling Enabled by a Redox-Active Ligand

Roman G. Belli, Victoria C. Tafuri, Matthew V. Joannou, Courtney C. Roberts

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)3094-3099
Number of pages6
JournalACS Catalysis
Volume12
Issue number5
DOIs
StatePublished - Mar 4 2022

Bibliographical note

Funding Information:
Financial support was provided by the University of Minnesota and the Petroleum Research Fund of the American Chemical Society (ACS PRF 62432-DNI1).

Publisher Copyright:
© 2022 American Chemical Society.

Keywords

  • alkyl-alkyl bonds
  • cross-coupling
  • redox-active ligands
  • scandium catalysis

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