Table 4.
Library data for compound 11{146–167}.
| compound | isocoumarin | reactant | methoda | yieldb (%) | purityc (%) |
|---|---|---|---|---|---|
| 11{146} | 11{83} | 12{2} | A | 80 | >99 |
| 11{147} | 11{83} | 12{3} | A | 79 | >99 |
| 11{148} | 11{83} | 12{17} | A | 69 | 95 |
| 11{149} | 11{83} | 12{18} | A | 45 | 92 |
| 11{150} | 11{83} | 12{19} | A | 62 | 99 |
| 11{151} | 11{84} | 12{2} | A | 77 | >99 |
| 11{152} | 11{84} | 12{3} | A | 58 | 91 |
| 11{153} | 11{84} | 12{10} | A | 70 | >99 |
| 11{154} | 11{84} | 12{16} | A | 14 | 92 |
| 11{155} | 11{84} | 12{17} | A | 54 | >99 |
| 11{156} | 11{84} | 12{18} | A | 59 | 96 |
| 11{157} | 11{84} | 12{19} | A | 21 | >99 |
| 11{158} | 11{85} | 12{2} | A | 58 | >99 |
| 11{159} | 11{85} | 12{3} | A | 53 | >99 |
| 11{160} | 11{85} | 12{18} | A | 58 | 94 |
| 11{161} | 11{85} | 12{19} | A | 58 | >99 |
| 11{162} | 11{86} | 12{18} | A | 45 | 99 |
| 11{163} | 11{86} | 12{19} | A | 58 | 99 |
| 11{164} | 11{83} | 13{1} | B | 47 | >99 |
| 11{165} | 11{86} | 13{1} | B | 10 | >99 |
| 11{166} | 11{84} | 14{2} | C | 26 | >99 |
| 11{167} | 11{86} | 14{1} | C | 69 | >99 |
a
Method A: alkyne (1.5 equiv), PdCl2(PPh3)2 (3 mol %), CuI (2 mol %), 3:1 DMF/Et3N, 60 °C; Method B: boronic acid (1.5 equiv), Pd(PPh3)4 (5 mol %), Cs2CO3 (2 equiv), 1.5:0.3:0.2 DMF/EtOH/H2O, microwave irradiation, 120 °C; Method C: styrene (2 equiv), Pd(OAc)2 (15 mol %), Na2CO3 (2.5 equiv), TBAC (1 equiv), DMF, 80 °C.
b
Isolated yield after preparative HPLC.
c
UV purity determined at 214 nm after preparative HPLC.