Table 1.
Reaction optimizationa
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---|---|---|---|---|
Entry | Additive | OR′ | R | Yield [%] |
1 | — | OAc | Ac | 11 |
2 | — | OAc | COCF3 | 21 |
3 | — | OAc | Ts | 13 |
4 | — | OTs | Ts | 10 |
5 | — | O2CCF3 | COCF3 | 22 |
6 | 1 equiv. AcOH | OAc | Ac | 29 |
7 | 5 mol% AgOAc | OAc | Ac | 27 |
8 | 1 equiv. AcOH | O2CCF3 | COCF3 | 17 |
9 | 5 mol% AgOAc | O2CCF3 | COCF3 | 22 |
10 | 1 equiv. AcOHb | OAc | Ac | 0 |
Conditions: benzene (0.50 mL, 5.6 mmol, 40 equiv.), Pd(OAc)2 (3.1 mg, 14 μmol, 10 mol%), 1 (2.5 mg, 14 μmol, 10 mol%), RNH–OR′ (140 μmol, 1.0 equiv.), 100 °C, 24 h.
No Pd catalyst.