Optimization of the reaction conditionsa.
Entry | Acid | Solvent | Yieldsb (%) | |
---|---|---|---|---|
2a | 3a | |||
1 | TMSOTf | DCM | 50 | 44 |
2 | TMSOTf | Toluene | 48 | 43 |
3 | TMSOTf | THF | 56 | 33 |
4 | TMSOTf | MeCN | 44 | <5 |
5 | AgOTf | DCM | 44 | 17 |
6c | (CuOTf)2·toluene | DCM | N.R. | N.R. |
7 | Cu(OTf)2 | DCM | 58 | 15 |
8 | Sc(OTf)3 | DCM | 52 | 24 |
9 | Bi(OTf)3 | DCM | 47 | 30 |
10 | Fe(OTf)3 | DCM | 52 | 30 |
11 | In(OTf)3 | DCM | 62 | 20 |
12 | Ac2O | DCM | N.R. | N.R. |
13 | AlCl3 | DCM | 23 | __d |
14 | BF3·OEt2 | DCM | 31 | 20 |
15 | AcOH | DCM | 52 | 20 |
16 | TfOH | DCM | 50 | 23 |
17c | p-TsOH | DCM | N.R. | N.R. |
Reaction conditions: 1a (1.0 mmol), HMDS (0.5 mL, 2.4 mmol), acid (0.5 mmol), solvent (2 mL), MW (150 °C), 0.5 h.
Isolated yields.
No reaction occurred.
Unknown products were obtained.