Organocatalyst for Electrophilic Halogenation of Aromatic Compounds under Mild Conditions

Halogen groups are one of the most important functional groups in synthetic chemistry. They act as a starting point for functional group transformations. On the other hand, a halogenation reaction with high selectivity and reactivity still remains a challenge. Nishii and Miura et al. developed an organocatalyst called Trip-SMe for the electrophilic halogenation of aromatic C-H bond.¹⁾ In the presence of Trip-SMe and a cocatalyst, halogenation of aromatic compounds with N-halosuccinimides proceeds regioselectively under mild conditions. In addition, Trip-SMe can be applied for trifluoromethylthiolation of aromatic compounds.²⁾

Related Products

D6031

Trip-SMe

B0656

N-Bromosuccinimide

C0291

N-Chlorosuccinimide

S0463

Silver Hexafluoroantimonate(V)

T0751

Trifluoromethanesulfonic Acid

References

• 1) Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides
  • Y. Nishii, M. Ikeda, Y. Hayashi, S. Kawauchi, M. Miura, J. Am. Chem. Soc. 2020, 142, 1621.
• 2) Metal-Free Direct Trifluoromethylthiolation of Aromatic Compounds Using Triptycenyl Sulfide Catalyst
  • R. Kurose, Y. Nishii, M. Miura, Org. Lett. 2021, 23, 2380.

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