Table 2. Screening of the Model Reaction in Various Solventsa.
| entry | solvent | yield (%) |
|---|---|---|
| 1 | DMF | 94 |
| 2 | EtOH | – |
| 3 | DCE | 73 |
| 4 | ACN | 86 |
Reaction conditions: 1a (0.1 mmol), 2 (0.1 mmol), 3 (0.25 mmol), 4 (0.35 mmol), Sc(OTf)3 (20 mol %), dry solvent (2 mL) 70 °C, N2 atmosphere. DMF = N,N-dimethylformamide. DCE = 1,2-dichloroethane. ACN = acetonitrile. It is noteworthy that the presence of solid potassium carbonate as a base in dry pyridine did not affect the global yield when the reaction was performed at a gram scale (Table 1, entry 9). Finally, the reaction performed equally well with ScBr3 as a catalyst (Table 1, entry 10). Using the optimized conditions [20% Sc(OTf)3], the protocol was extended to substrates 1b–l, starting from commercially available isatins subjected to N-alkylation29 (Table 3).