Table 1.
Optimization of the conditions for the reaction between 1a, 2a, and 3a.a
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| entry | catalyst | solvent | yield (%)b |
| 1 | — | 1,4-dioxane | 0 |
| 2 | Bi(OTf)3 | 1,4-dioxane | 36 |
| 3 | AlCl3 | 1,4-dioxane | 80 |
| 4 | FeCl3 | 1,4-dioxane | 44 |
| 5 | NiCl2 | 1,4-dioxane | 21 |
| 6 | PTSA | 1,4-dioxane | 73 |
| 7 | HOAc | 1,4-dioxane | trace |
| 8 | AlCl3 | EtOH | 31 |
| 9 | AlCl3 | MeCN | 50 |
| 10 | AlCl3 | PhMe | 27 |
| 11 | AlCl3 | DMSO | 62 |
| 12c | AlCl3 | 1,4-dioxane | 55 |
| 13d | AlCl3 | 1,4-dioxane | 51 |
| 14e | AlCl3 | 1,4-dioxane | 40 |
| 15f | AlCl3 | 1,4-dioxane | 72 |
a1a: 0.5 mmol, 2a: 0.6 mmol, 3a: 0.6 mmol, catalyst: 0.05 mmol, solvent: 1 mL, 80 °C, 6 h. bIsolated yield, calculated with respect to 1a. cAlCl3: 0.025 mmol. d50 °C. e2 h. f10 mmol-scale reaction.
