Optimization of the reaction conditionsa.
![]() | |||||
---|---|---|---|---|---|
Entry | Solvent | Oxidant | Time (h) | Temp (°C) | Yield (%) |
1 | DMSO | SF | 24 | 100 | 71, 15b, 65c |
2 | DMF | SF | 24 | 100 | 23 |
3 | DMAC | SF | 24 | 100 | Trace |
4 | Toluene | SF | 24 | 100 | 0 |
5 | NMF | SF | 24 | 100 | 18 |
6 | DMSO | (NH4)2S2O8 | 24 | 100 | Trace |
7 | DMSO | K2S2O8 | 24 | 100 | 33 |
8 | DMSO | — | 24 | 100 | 0 |
9 | DMSO | SF | 48 | 100 | 73 |
10 | DMSO | SF | 16 | 100 | 46 |
11 | DMSO | SF | 8 | 100 | 23 |
12 | DMSO | SF | 4 | 100 | Trace |
13 | DMSO | SF | 24 | 120 | 67 |
14 | DMSO | SF | 24 | 80 | 56 |
15 | DMSO | SF | 24 | 60 | 29 |
16 | DMSO | SF | 24 | 40 | 0 |
Reaction conditions: 1a (1 mmol), 2 (1 mmol), oxidant (1.1 mmol) and DMSO (3 mL) in a sealed tube at the indicated reaction conditions.
Reaction under N2.
Reaction was performed on a 10 mmol scale of 1a.