Table 1 Tandem Suzuki coupling/transfer hydrogenation of 4-bromoacetophenone and phenylboronic acid.
| ||||||
|---|---|---|---|---|---|---|
Entry | Cat. | ROH | Base | \(\hbox {Yield}^{\mathrm{a}}\) | ||
A | B | C | ||||
1 | 5 | \(i\hbox {PrOH}\) | NaOH | 0 | Trace | 90 |
2 | 5 | \(i\hbox {PrOH}\) | KOH | Trace | 0 | 85 |
3 | 5 | \(i\hbox {PrOH}\) | \(\hbox {KO}^{t}\hbox {Bu}\) | \(20^{*}\) | 10 | \(56^{*}\) |
4 | 5 | \(i\hbox {PrOH}\) | \(\hbox {Cs}_{2}\hbox {CO}_{3}\) | 0 | 93 | 0 |
5 | 5 | n-PrOH | NaOH | 0 | 45 | 10 |
6 | 5 | \(\hbox {PhCH}_{2}\hbox {OH}\) | NaOH | 0 | Trace | 0 |
7 | \(\mathbf{5+Hg}\) | iPrOH | NaOH | 0 | 0 | 15 |
8b | 3+4 | iPrOH | NaOH | 0 | 0 | 75 |
9c | 3 | \(i\hbox {PrOH}\) | NaOH | 65 | 0 | \(25^{*}\) |
10c | 4 | \(i\hbox {PrOH}\) | NaOH | 76 | 0 | \(15^{*}\) |
11c,d | 2 | \(i\hbox {PrOH}\) | NaOH | 30 | 0 | 0 |
12c,d | 1 | \(i\hbox {PrOH}\) | NaOH | 90 | 0 | 0 |
