Fro-DO: Novel Ligand for Quaternary Carbon-Carbon Coupling

Introduction

Successful ligands that electronically facilitate elementary yet vital steps of the catalytic cycle, such as the bond-forming reductive elimination step, are underdeveloped. The major ligand classes associated with transition metal catalysis are predominantly σ-donating in character, including phosphines, amines, and NHCs. In cross-coupling reactions, these ligands promote oxidative addition by rendering the metal catalyst electron rich.

Herein, we introduce a novel electron-deficient olefin ligand, Fro-DO (804371). Fro-Do has enabled the generation of quaternary centers by Ni-catalyzed cross coupling with aziridines. Along with Abby Doyle’s group at Princeton, Sigma-Aldrich is proud to introduce a revolutionary new ligand for Ni-catalyzed synthesis.

Representative Schematic

Advantages

  • A new class of ligand that is electronically and structurally distinct from conventional ligand classes
  • Expected to promote novel reactivity
  • Bench stable crystalline solid that can be easily weighed out

For more on Abby Doyle’s nickel-based transition-metal catalysis, visit her Professor Product Portal.

Special thanks to Mr. Dennis Huang for contributing this technology spotlight.

Materials

     
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