Molecular Formula
C20H18N2O2
Smiles
C(NC1=C2C(C=CC=C2)=CC=C1C)(=O)C(NCC1=CC=CC=C1)=O
General Description
MNBO is a highly active N,N'-alkyl oxalamide ligand for copper-catalyzed C–N cross-coupling. In the presence of Cu₂O as a copper precursor and at extremely low copper loadings, it affords the highly efficient coupling of (hetero)aryl bromides and iodides with primary amines, aqueous ammonia, and cyclic secondary amines.
Application
MNBO enables a robust, scalable, and green synthetic route to structurally diverse (hetero)aryl amines. The protocol is well suited to the construction of C–N bonds in the late-stage functionalization of pharmaceutical intermediates, agrochemicals and fine chemical synthesis.
Gao J, et al. disclosed an efficient Cu-catalyzed aryl amination, catalyzed by newly developed N-(naphthalen-1-yl)-N′-alkyl oxalamide ligands (MNBO and related amides). In the presence of 0.01-0.1 mol % Cu₂O and ligand, (hetero)aryl iodides or bromides smoothly coupled with primary amines or aqueous ammonia at 50-80 ℃, with up to 10,000 turnovers. The system is compatible with a wide substrate scope, including functionalized amines, heteroaryl halides and cyclic secondary amines with excellent chemoselectivity. The protocol provides mild, scalable and environmentally friendly access to (hetero)aryl amines, surpassing the catalytic efficiency of previous Cu-based systems.
Fig. 1 MNBO enhances Cu-catalyzed aryl halide-amine coupling. (Gao J.; et al. 2017)
References
- Gao J, et al. Discovery of N-(naphthalen-1-yl)-N′-alkyl oxalamide ligands enables Cu-catalyzed aryl amination with high turnovers. Organic Letters, 2017, 19(11): 2809-2812.
What type of reaction is the MNBO ligand used for?
It varies by product. Please contact us for details.
Do you offer custom packaging?
Yes, we can customize packaging and specifications to your needs.
What is the MOQ of MNBO ligand?
Our MOQs are product-dependent. Please contact us to determine the specific MOQ for the MNBO.
What purity/packaging options are available?
We have various purity and packaging specifications. Please contact us to discuss options to fit your R&D or production needs.
How does the MNBO ligand compare to the traditional Cu-catalyzed system?
MNBO ligands significantly outperform previously reported systems in terms of catalytic efficiency, substrate scope, and chemoselectivity.
