Table 3.
C-arylation of acetylacetone using different aryl halidesa
Entry | Aryl halide | Product | Time (h) | Yieldb (%) |
1 | iodobenzene | 3-phenylpentane-2,4-dione | 8 | 80 |
2 | bromobenzene | 3-phenylpentane-2,4-dione | 10 | 79 |
3 | p-nitroiodobenzene | 3-(4-nitrophenyl)-pentane-2,4-dione | 6 | 83 |
4 | p-methyliodobenzene | 3-p-tolylpentane-2,4-dione | 10 | 78 |
5 | m-trifluoromethyliodobenzene | 3-(3-trifluromethyl-phenyl)-pentane-2,4-dione | 7 | 81 |
6 | 1-iodo-2-methylbenzene | 3-o-tolyl-pentane-2,4-dione | 11 | 76 |
7 | 1-iodo-4-methoxybenzene | 3-(4-methoxy-phenyl)-pentane-2,4-dione | 12 | 75 |
aReaction conditions: acetylacetone (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.