Table 4.
C-arylation of diethyl malonate using different aryl halidesa.
Entry | Aryl halide | Product | Time (h) | Yieldb (%) |
1 | iodobenzene | 2-phenylmalonic acid diethylester | 9 | 78 |
2 | bromobenzene | 2-phenylmalonic acid diethylester | 11 | 76 |
3 | p-nitroiodobenzene | 2-(4-nitrophenyl)-malonic acid diethylester | 6 | 81 |
4 | p-methyliodobenzene | 2-p-tolylmalonic acid diethylester | 12 | 76 |
5 | m-trifluoromethyliodobenzene | 2-(3-trifluromethyl-phenyl)-malonic acid diethylester | 7 | 80 |
6 | 1-iodo-2-methylbenzene | 2-o-tolylmalonic acid diethylester | 13 | 75 |
7 | 1-iodo-4-methoxybenzene | 3-(4-methoxy-phenyl)-malonic acid diethylether | 14 | 74 |
aReaction conditions: diethyl malonate (3 mmol), aryl halide (1 mmol), 10 mol % CuO-nanoparticles, Cs2CO3 (0.5 mmol), DMSO; temperature 80 °C; N2; 1 atm.
bIsolated and optimized yields.