Optimization of the reaction conditionsa.
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Entry | Solvent | Yield (%) |
1 | MeCN | 90 |
2 | DCE | 61 |
3 | DMC | 86 |
4 | PC | Trace |
5 | H2O | 80 |
6 | 2-CH3-THF | 42 |
7 | EG | 19 |
8 | TBME | 57 |
9 | PEG-200 | Trace |
10 | PEG-400 | Trace |
11 | H2O : EtOH (v/v = 1 : 1) | 77 |
12 | H2O : EtOH (v/v = 2 : 1) | 70 |
13 | H2O : MeOH (v/v = 1 : 1) | 78 |
14 | H2O : MeOH (v/v = 2 : 1) | 72 |
15 | H2O : THF (v/v = 1 : 1) | 61 |
16 | H2O : THF (v/v = 2 : 1) | 68 |
17b | H2O | N.D. |
18c | H2O | N.D. |
19d | H2O | 74 |
Reaction conditions: 1a (0.2 mmol), 2a (0.4 mmol), PIDA (0.4 mmol), solvent (2 mL) under air for 8 h, rt, 430 nm Blue LED (5 W). N.D. = Not detected. Isolated yields were given. DCE = 1,2-dichloroethane, DMC = dimethyl carbonate. TBME = tert-butyl methyl ether, EG = ethylene glycol, PC = propylene carbonate.
Without PIDA.
Experiment performed in the dark.
Reaction under N2 atmosphere.