Table 1.
Entry | Cat (20 mol%) | Reagent | Oxidant | Solvent (1 mL/1 mL) | Yield (%)a |
---|---|---|---|---|---|
1 | AgNO3 | A | PIDA | CH3CN/H2O | Trace |
2 | AgNO3 | A | Oxone | CH3CN/H2O | Trace |
3 | AgNO3 | A | Na2S2O8 | CH3CN/H2O | 37 |
4 | AgNO3 | A | K2S2O8 | CH3CN/H2O | 40 |
5 | AgNO3 | A | K2S2O8 | Acetone/H2O | 55(71)b |
6 | – | A | K2S2O8 | Acetone/H2O | n.d. |
7 | AgI | A | K2S2O8 | Acetone/H2O | Trace |
8 | CuCl2 | A | K2S2O8 | Acetone/H2O | Trace |
9 | FeCl2 | A | K2S2O8 | Acetone/H2O | Trace |
10 | MnBr2 | A | K2S2O8 | Acetone/H2O | Trace |
11 | AgNO3 | A | K2S2O8 | PhCF3/H2O | n.d. |
12 | AgNO3 | A | K2S2O8 | DMSO/H2O | Trace |
13 | AgNO3 | B | K2S2O8 | Acetone/H2O | 32 |
14 | AgNO3 | C | K2S2O8 | Acetone/H2O | 54 |
15 | AgNO3 | D | K2S2O8 | Acetone/H2O | 37 |
Reaction conditions: 1a (0.2 mmol), catalyst (0.04 mmol), oxidant (0.3 mmol), reagent (0.4 mmol), solvent (2 mL), stirred at 50 °C under Ar (1 atm) for 24 h
aIsolated yield
bYield based on recovered alcohols