Molecular Formula
C20H24N2O8
Smiles
C(NC1=C(OC)C=C(OC)C=C1OC)(=O)C(NC1=C(OC)C=C(OC)C=C1OC)=O
Relative Density
1.283±0.06
General Description
BTMPO is a highly efficient bisoxalamide ligand that is specifically developed to tackle the long-standing challenge of copper-catalyzed coupling of (hetero)aryl bromides with sterically hindered acyclic secondary amines. Outperforming other bisoxalamide ligands, it allows efficient C–N bond formation under mild conditions, suppressing side reactions.
Application
BTMPO facilitates the efficient synthesis of sterically demanding tertiary amines by allowing couplings with either hindered nucleophiles or less reactive (hetero)aryl bromides. It enables a broader range of accessible substrates and is particularly suited for the synthesis of complex amine structures that are unobtainable with traditional methods, in support of sustainable development.
The coupling of (hetero)aryl bromides with sterically hindered acyclic secondary amines is a long-standing challenge in Cu-catalyzed amination. Compared to other bisoxalamide ligands, BTMPO provides superior performance in these difficult transformations, enabling good to excellent yields under relatively mild conditions (80 ℃, 1-2 mol % CuI and ligand).
BTMPO suppresses side product formation and allows efficient coupling of substrates with increased steric hindrance or reduced nucleophilicity. The scope of the reaction is broad, covering a variety of (hetero)aryl bromides and functionalized acyclic secondary amines, including those with hydroxyl or aryl groups, with excellent chemoselectivity.
Fig. 1 BTMPO effectively enables Cu-catalyzed N-arylation. (Bhunia S.; et al. 2017)
References
- Bhunia S, et al. N, N′-Bisoxalamides enhance the catalytic activity in Cu-catalyzed coupling of (Hetero) Aryl bromides with anilines and secondary amines. The Journal of Organic Chemistry, 2017, 82(23): 12603-12612.
What is BTMPO used for?
BTMPO enables efficient Cu-catalyzed C-N coupling of (hetero)aryl bromides with sterically hindered secondary amines.
What is the Minimum Order Quantity (MOQ) for BTMPO?
Our MOQ varies by product. Please contact us for specific details.
What packaging options are available for your BTMPO?
Various packaging options are available. Contact us for specifications.
What is the key advantage of using BTMPO?
BTMPO significantly suppresses side reactions, enabling the high-yield synthesis of sterically demanding tertiary amines that are difficult to access with other ligands.
