Table 1.
Suzuki-Miyaura Cross-Coupling of Various Aryl Halides with Dioxolanylethyltrifluoroborate 1 a
| |||
|---|---|---|---|
| entry | electrophile | product | isolated yield (%) |
| 1 |
|
|
89 (Br) 82b (Br) 74 (Cl) |
| 2 |
|
|
56 |
| 3 |
|
|
83 |
| 4 |
|
|
48 (Br) 0c (Cl) |
| 5 |
|
|
70 |
| 6 |
|
|
62 |
| 7 |
|
|
90 |
| 8 |
|
|
38 (Br) 82 (Cl) |
| 9 |
|
|
59 |
| 10 |
|
|
71 (Br) 55 (Cl) |
| 11 |
|
|
50d |
| 12 |
|
|
68d |
| 13 |
|
|
69 |
| 14 |
|
|
38e |
Reaction conditions: Aryl halide (1.0 equiv), organotrifluoroborate (1.1 equiv), PdCl2AtaPhos2 (5 mol %), Cs2CO3 (3.0 equiv), toluene/H2O (4:1, [ ] = 0.25 M), 100 °C, 14 h.
Using 2.5 mol % catalyst.
A mixture of aryl chloride and boronic acid was recovered.
Product contains up to 8 % impurity.
Reaction performed on a 3 mmol scale using a 1 : 1 trifluoroborate/electrophile ratio and only 1 mol % Pd.