Comparison of forward-order and reverse-order strategies in synthesis of unsymmetrical biaryl compoundsa.
| |||||
|---|---|---|---|---|---|
| Entry | Ar1–Cl | Ar2–Cl | Product | Forward yieldb (%) | Reverse yieldb (%) |
| 1 |
|
|
|
87 | 98 |
| 2 |
|
|
|
84 | 25 |
| 3 |
|
|
|
65 | 93 |
| 4 |
|
|
|
91c | 20 |
| 5 |
|
|
|
77c | 42c |
| 6 |
|
|
|
38d | 79c |
| 7 |
|
|
|
35c | 85c |
General conditions: (a) first chloride (1.1 equiv.), XPhos-Pd-G2 (1.0 mol%), XPhos (1.0 mol%), B2pin2 (1.2 equiv.), K3PO4·7H2O (3.0 equiv.), EtOH (0.275 M), RT, 2 h; (b) second chloride (1.0 equiv.), 3.0 M aq. K3PO4·7H2O (3.0 equiv.), RT, 8 h.
Yield of isolated product.
15 h for the second step.
6 h for the second step.