Table 1. Influence of the ligand on the product distribution a .
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Entry | L | 4a b (%) | 15 b (%) | 14a b (%) | 14b b (%) |
1 | tBu3P | 4 | <1 | 59 | 21 |
2 | PCy3 | 58 | 30 | 8 | — |
3 | PPh3 | 40 | 40 | 11 | — |
4 | L2 | 63 | 33 | <1 | — |
5 | L3 | 12 | 40 | 28 | 8 |
aReaction conditions: 0.05 mmol 3a, 2.5 mol% Pd(dba)2, 5.0 mol% L, 20 mol% AdCO2H, 1.5 equiv. Cs2CO3 0.25 M in toluene, 110 °C, 12 h.
bDetermined by 1H-NMR with an internal standard.