Optimization of reaction conditionsa.
Entry | Deviation from above | Yieldb (%) |
---|---|---|
1 | None | <5 |
2 | Toluene/H2O (9 : 1) as solvent | 44 |
3 | 10 mol% of DIPEA | 59 |
4 | 5 mol% of thiophenol | 40 |
5 | 20 mol% of thiophenol | 60 |
6 | NaHCO3 instead of DIPEA | 57 |
7 | Two blue LEDs (∼450 nm, 7 W) | 61 |
8 | No photocatalyst | 0 |
9 | No base | 0 |
10 | No thiophenol | 11 |
11 | Open atmosphere | 34 |
12 | Argon atmosphere | 77 |
13 | Oxygen atmospherec | 12 |
Reactions carried out on a 0.2 mmol scale in N2-sparged solvents [0.1 M] at ambient temperature for 24 h.
Yields determined by GC-MS using hexadecane as internal standard.
The yield of oxygenated by-products was 60%.