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N-Acylation of Indole with Hydrocinnamaldehyde
| entry | oxidant | additive | 9a:8 | solventa | yield (%)b |
|---|---|---|---|---|---|
| 1 | MnO2 | none | 10:1 | toluenec | 12 |
| 2 | PCC | none | 10:1 | toluenec | 16 |
| 3 | TPAP/NMO | 4 Å mol. sieves | 10:1 | CH2Cl2 | 4 |
| 4 | TPAP/NMO | 4 Å mol. sieves | 10:1 | CH3CN | 15 |
| 5 | TPAP/NMO | 4 Å mol. sieves | 5:1 | CH3CN | 36 |
| 6 | TPAP/NMO | 4 Å mol. sieves | 1:1 | CH3CN | 18 |
| 7 | TPAP/NMO | 4 Å mol. sieves | 1:1 | CH3CNd | 81(74) |
at 25 °C with 9a at 0.33 M.
yields calculated by GC (isolated yield in parentheses).
at 100 °C
9a at 0.6 M
