MNFO
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MNFO is a second-generation oxalic diamide ligand for copper-catalyzed Ullmann-type C-N cross-coupling reactions. With MNFO, amination of (hetero)aryl bromides can be achieved using aqueous ammonia under extremely low catalyst loadings (typically 0.001 equiv CuI and 0.001 equiv MNFO, resulting in turnover numbers (TONs) up to 9,500). The reaction takes place at 80 ℃ in ethanol, and produces the corresponding primary arylamines in >90 % yield without the inert atmosphere or drying.
MNFO is significantly more active and efficient than first-generation ligands, particularly less reactive aryl bromides. It is thought that the furan rings promote copper coordination and stabilize the Cu(I)/Cu(III) catalytic cycle. The ligand was demonstrated on a multihundred-millimole scale, and only milligram quantities of copper and ligand are needed, making it a low-cost reagent that does not place as much burden on downstream metal removal, and therefore a good candidate for industrial-scale processes in pharmaceutical and agrochemical production.
Fig. 1 Cu-mediated Ullmann-type transformations. (Yang Q.; et al. 2022)
References
- Yang Q, et al. Cu-mediated Ullmann-type cross-coupling and industrial applications in route design, process development, and scale-up of pharmaceutical and agrochemical processes. Organic Process Research & Development, 2022, 26(6): 1690-1750.
