Powerful Ligand for C-H Borylation of Electron-Rich Arenes

The C-H borylation reaction of pinacolborane (HBpin) with arenes is a clean reaction with only hydrogen gas as the byproduct and is catalyzed by an iridium complex and a bipyridine ligand. However, conventional bipyridine ligands exhibit insufficient activity in reactions with electron-rich arenes. SpiroBpy (1) has recently been reported to efficiently promote C-H borylation reactions with a small amount of catalyst for electron-rich arenes.¹⁾ The CH-π interaction between the C-H bond of 1 and the π-electrons of the substrate is considered to be important for its high catalytic activity.
Furthermore, a derivative of 1, SpiroBpy-Bpin, has been used as a ligand for meta-selective C-H borylation on substituted arenes.²⁾ New SpiroBpy derivatives to catalyze C-H borylation reactions of a pyridine ring have also been reported.³⁾

References

• 1) Noncovalent interaction with a spirobipyridine ligand enables efficient iridium-catalyzed C–H activation
  • Y. Jin, B. Ramadoss, S. Asako, L. Ilies, Nat. Commun. 2024, 15, 2886.
• 2) Remote steric control for undirected meta-selective C-H activation of arenes
  • B. Ramadoss, Y. Jin, S. Asako, L. Ilies, Science 2022, 375, 658.
• 3) Spirobipyridine Ligands as a Unique Platform for Substrate Recognition and Reaction Control through Noncovalent Interactions
  • S. Asako, L. Ilies, ACS Catal. 2025, 15, 6372.

Related Products

C2662

1,5-Cyclooctadiene)(methoxy)iridium(I) Dimer (= [IrOMe(cod)]₂)

T2572

Pinacol Borane (= HBpin)

B6552

SpiroBpy-Bpin

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