Table 1. Optimization of amidation reaction conditionsa.
| ||
|---|---|---|
| Entry | Deviation from standard conditions | Yield of 3a (%) |
| 1 | None | 87 |
| 2 | PPTA-RSS instead of the PPTA-RSS system | 34 |
| 3 | EY instead of the PPTA-RSS system | 16 |
| 4 | RhB instead of the PPTA-RSS system | 28 |
| 5 | SR101 instead of the PPTA-RSS system | Trace |
| 6 | Cy5 instead of the PPTA-RSS system | Trace |
| 7 | PPTA-RSS + EY instead of the PPTA-RSS system | 43 |
| 8 | PPTA-RSS + EY + RhB instead of the PPTA-RSS system | 48 |
| 9 | PPTA-RSS + EY + RhB + SR101 instead of the PPTA-RSS system | 56 |
| 10 | N2 instead of air | ND |
| 11 | O2 instead of air | 88 |
| 12 | 365 nm instead of 395 nm | 89 |
| 13 | 425 nm instead of 395 nm | 78 |
| 14 | No light | ND |
| 15 | No PC | ND |
Standard conditions: benzaldehyde (0.3 mmol), pyrrolidine (0.45 mmol), PPTA-RSS + EY + RhB + SR101 + Cy5 (1 mol%), H2O (2.0 mL), irradiated with a 395 nm LED at room temperature for 24 h. Yields were determined by isolated yield. PC, photocatalyst; RT, room temperature; ND, not detected.