Molecular Formula
C10H11NO3
Smiles
O=C(C(O)=O)NC1=C(C)C=CC=C1C
Appearance
White to off-white powder
Relative Density
1.290±0.06
General Description
DMPAO (2,6-Dimethylanilino(oxo)acetic acid) is a uniquely powerful and inexpensive ligand specifically developed for copper-catalyzed N-arylation reactions. DMPAO has exceptional catalytic performance and broad substrate compatibility including primary amines, cyclic secondary amines, and various aryl halides while maintaining excellent functional group tolerance.
Application
DMPAO enables efficient synthesis of tertiary anilines through copper-catalyzed N-arylation of amines with aryl halides, demonstrating particular effectiveness with challenging substrates like acyclic secondary aliphatic amines and functionalized amines containing hydroxyl groups.
DMPAO is a highly potent, low-cost ligand for copper-catalyzed N-arylation of amines. The optimized conditions of 10 mol % CuI, 20 mol % DMPAO, K3PO4, DMSO, 60-110 ℃ allow the coupling of aryl halides with acyclic secondary aliphatic amines. Excellent results are obtained with primary amines and cyclic secondary amines at catalyst loadings as low as 1 mol % CuI/2 mol % DMPAO with complete conversion in 24 h at 90 ℃, performance which is superior to that obtained with any other common ligand.
Crystallographic precedent suggests DMPAO can coordinate with Cu(II) through the amidate nitrogen as well as the carboxylate oxygen. A catalytic cycle is proposed by Zhang Y et al. The high electron density and dianionic nature of DMPAO is thought to promote the oxidative addition and reductive elimination steps.
Fig. 1 DMPAO for CuI-catalyzed N-arylation. (Zhang Y.; et al. 2012)
References
- Zhang Y, et al. CuI/DMPAO-catalyzed N-arylation of acyclic secondary amines. Organic Letters, 2012, 14(12): 3056-3059.
What is DMPAO used for?
DMPAO is used to efficient Cu-catalyzed N-arylation of amines with aryl halides.
What are the main advantages of DMPAO?
High efficiency, with challenging amines, low cost, and unmatched performance.
How does DMPAO compare to traditional ligands?
DMPAO significantly outperforms N,N-dimethylglycine, L-proline, and phenanthroline.
What is the minimum order quantity for DMPAO?
MOQ varies. Please contact us for details.
Can DMPAO be used in academic research?
Yes, DMPAO is suitable for both research and industrial applications.
