Table 1.
Select optimization results for the hydroalkylation reactiona.
 | ||||
|---|---|---|---|---|
| Entry | H-source | Equiv. H-source | t (h) | In situ yield 1 (%) |
| 1 | IPA | 3 | 24 | 16 |
| 2 | MeOH | 3 | 24 | 11 |
| 3 | AcOH | 3 | 24 | 15 |
| 4 | PhSH | 1 | 24 | 0 |
| 5 | PhOH | 1 | 24 | 16 |
| 6 | PhOH | 3 | 24 | 23 |
| 7 | PhOH | 3 | 36 | 42 |
| 8 | 2-MeO-PhOH | 3 | 36 | 84 |
| 9 | 2-MeO-PhOH | 3 | 48 | >99 |
| 10 | 4-CF3-PhOH | 3 | 48 | 51 |
| 11 | 4-Cl-PhOH | 3 | 48 | 70 |
| 12 | 4-Me-PhOH | 3 | 48 | >99 |
| 13 | 4-MeO-PhOH | 3 | 48 | >99 |
aConditions: 1,1-diphenylethylene (0.1 mmol, 1.0 equiv), BnBF3K (1.5 equiv), [Ir(dF(CF3)ppy)2(dtbbpy)][PF6] (1 mol%), H-source, DMF, r.t., 24 W blue LED light; GC yield reported with reference to 1-methylnaphthalene as an internal standard.