Table 2. Optimization of the transition metal-catalyzed hydroalkoxylation of the Michael adduct 3a a .
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Entry | Catalyst | Solvent | t (h) | Yield b (%) |
1 | PPh3AuCl/AgNTf2 | Toluene | 0.25 | 99 |
2 | AgNO3 | CH2Cl2 | 3.5 | 97 |
3 | AgNTf2 | CH2Cl2 | 5 | 99 |
4 | AgBF4 | CH2Cl2 | 3 | 97 |
5 | Ag2O | CH2Cl2 | >96 | 69 |
6 | Ag2CO3 | CH2Cl2 | 2 | 99 |
7 | TFA | CH2Cl2 | >24 | Traces |
8 | CuI | CH2Cl2 | >24 | Traces |
9 | PtCl2 | CH2Cl2 | >24 | Traces |
aReaction conditions: 0.10 mmol of 3a, 10 mol% of catalyst, solvent 0.5 mL, rt.
bYield of isolated 4a after flash chromatography.