Table 1.
Comparison of Ni-H and Co-H catalyzed enantioselective anti-Markovnikov hydroalkylation of alkenesa
| Entry | Metal salt | Solvent | Yield (%) | er |
|---|---|---|---|---|
| 1 | NiBr2·DME | DME | 9 | 69:31 |
| 2 | NiBr2·DME | THF | trace | N.D. |
| 3 | NiBr2·DME | DMA | trace | N.D. |
| 4 | NiBr2·DME | DMF | trace | N.D. |
| 5 | CoBr2·DME | DME | 98 | 95:5 |
| 6 | CoBr2·DME | THF | 75 | 95:5 |
| 7 | CoBr2·DME | DMA | 48 | 57:43 |
a 1a (0.10 mmol), 2a (0.20 mmol, 2.0 equiv), metal salt (10 mol%), L6 (15 mol%), CsF (0.20 mmol, 2.0 equiv), DEMS (0.20 mmol, 2.0 equiv), solvent (0.5 mL, 0.2 M), 0 °C, 24 h. Isolated yields. Er value was determined by chiral HPLC analysis. DEMS = diethoxymethylsilane.