Table 1.
Ligand effects in the palladium-catalyzed amidation of 4-bromo-1-methylimidazole.[a]
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Entry | Ligand | Conversion [%][b] | Yield [%][c] |
1 | L1 | <5 | 0 |
2 | L2 | <5 | 0 |
3 | L3 | 35 | 15 |
4 | L4 | <5 | 0 |
5 | L5 | 43 | 24 |
6 | L6 | 100 | 83 |
Reaction conditions: 4-bromo-1-methylimidazole (0.5 mmol), benzamide (1 mmol), [(allyl)PdCl]2 (0.75 mol%), ligand (3 mol%), Cs2CO3 (1 mmol), 2-methyl-2-butanol (1 mL), 90 °C, 21 h.
Determined by GC.
Yield of isolated product.