BFMO
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BFMO is a copper-catalyzed N-arylation ligand of (hetero)aryl bromides with anilines and secondary amines. BFMO allows high catalytic activity, enabling CuI loading as low as 0.5-5 mol% under mild conditions (80 ℃, EtOH) to achieve the reaction. This represents a significant advance over previously reported systems, which often required higher catalyst loading or harsher reaction conditions.
Pawar G G et al. demonstrates the broad substrate scope and high chemoselectivity of BFMO. The ligand smoothly promotes the coupling reaction of electron-rich, neutral, and even electron-deficient (hetero)aryl bromides with a wide range of anilines and cyclic secondary amines, including pharmaceutical relevant scaffolds. BFMO allows selective mono-arylation of piperazine, a widely used drug scaffold, preventing over-arylation.
The performance of BFMO in terms of yield, reaction rate, and functional group compatibility is superior to other investigated ligands. BFMO also suppresses the formation of side products resulting from competitive solvent insertion reactions such as ether formation. This is likely due to the bidentate coordination capability of the ligand and the electron-donating furan rings stabilizing the copper center and promoting reductive elimination.
Fig. 1 BFMO for Cu-catalyzed aryl halide–N-heterocycle coupling. (Pawar G G.; et al. 2017)
References
- Pawar G G, et al. Copper (I) Oxide/N, N′‐Bis [(2‐furyl) methyl] oxalamide‐Catalyzed Coupling of (Hetero) aryl Halides and Nitrogen Heterocycles at Low Catalytic Loading. Advanced Synthesis & Catalysis, 2017, 359(10): 1631-1636.
