Table 1.
Optimization of Pd Source.
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---|---|---|---|---|
entry | Pd source | additive | time | yieldb |
1. | Pd(nbd)Cl2 | none | 24 h | 7% |
2. | PdCl2 | none | 24 h | 27% |
3. | Pd(OAc)2 | none | 24 h | 76% |
4. | Pd(TFA)2 | none | 60 min | 87% |
5. | Pd(TFA)2 | Na2CO3 | 20 min | 95% |
6. | Pd(dba)3 | none | 24 h | 25% |
7. | Pd Black | none | 24 h | NR |
8. | None | none | 24 h | NR |
9. | Pd(TFA)2 | None, no O2 | 24 h | 24% |
10.c | Pd(TFA)2 | Na2CO3, Hg0 | 5 h | 84%d |
5 mol% Pd source, 20 mol% pyridine, 500 mg/mmol MS3Å, 1 atm O2, toluene (0.1M), 80 °C.
Isolated yield.
5 mol % (pyridine)2Pd(TFA)2, 10 mol% pyridine, 2 equiv Na2CO3, 30 equiv Hg0.
Conversion determined by GC.