Table 1. Optimization of Reaction Conditionsa.
| entry | additive | solvent | λ (nm) | conversion (%) |
|---|---|---|---|---|
| 1 | DPAP/MAP | CDCl3 | 0 | |
| 2b | CDCl3 | 0 | ||
| 3 | DPAP/MAP | EtOAc | 365 | 99 |
| 4 | DPAP | CDCl3 | 365 | 96 |
| 5 | MAP | CDCl3 | 365 | 94 |
| 6c | CDCl3 | 365 | 70 | |
| 7 | atm. O2 | EtOAc | 68 | |
| 8 | eosin Y | MeCN | 420 | 88 |
| 9 | acridine orange | CH2Cl2 | 420 | 41 |
| 10 | 9H-thioxanthen-9-one | CH2Cl2 | 420 | 86 |
Standard conditions: 0.1 M 1, DPAP (10 mol %), MAP (10 mol %), 2 h. Conversion measured by 1HNMR by integration of the product peak compared to the internal standard.
Inert atmosphere.
3 h reaction time.
