Ligand for the Synthesis of Biaryl Ethers

N¹,N²-Bis(2,5-dimethyl-1H-pyrrol-1-yl)oxalamide (1) is an oxalohydrazide type ligand which catalyzes the construction of biaryl ethers by forming a complex with copper salt.¹⁾ In the presence of the copper catalyst, biaryl ethers can be obtained in high yields by using aryl bromides and phenol derivatives as starting materials. The catalytic turnover number (TON) of the reactions is very high, reaching 8000 in some reactions. Furthermore, this reaction is tolerant to a wide variety of functional groups, so that it can be utilized in the latter step synthesis of biaryl ethers; even the compound 2 can be synthesized. In addition, the synthesis of aryl hydrazines has been reported using aryl bromides and hydrazine monohydrate under the similar conditions.²⁾

Related Products

B6291

N¹,N²-Bis(2,5-dimethyl-1H-pyrrol-1-yl)oxalamide

C2161

Copper(I) Bromide

H0081

Hexadecyltrimethylammonium Bromide

H0172

Hydrazine Monohydrate

References

• 1) Oxalohydrazide Ligands for Copper-Catalyzed C-O Coupling Reactions with High Turnover Numbers
  • R. Ray, J. F. Hartwig, Angew. Chem. Int. Ed. 2021, 60, 8203.
• 2) Facile and convenient synthesis of aryl hydrazines via copper-catalyzed C-N cross-coupling of aryl halides and hydrazine hydrate
  • D. V. Kurandina, E. V. Eliseenkov, P. V. Ilyin, V. P. Boyarskiy, Tetrahedron 2014, 70, 4043.

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