Table 1 Optimization of reaction conditionsa
From: Nickel-catalyzed regiodivergent hydrosilylation of α-(fluoroalkyl)styrenes without defluorination
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|---|---|---|---|---|---|---|
Entry | L | L (%) | Solvent | T/(oC) | Yield (%) | L:B (3a:4a) |
1 | — | — | toluene | 30 | 18 | >20:1 |
2 | PPh3 | 10 mol% | toluene | 30 | 17 | >20:1 |
3 | PPh3 | 5 mol% | toluene | 30 | 96 | >20:1 |
4 | PCy3 | 5 mol% | toluene | 30 | 38 | >20:1 |
5 | BPY | 5 mol% | toluene | 30 | <5 | — |
6 | 1,10-phen | 5 mol% | toluene | 30 | <5 | 7:1 |
7b | L1 | 5 mol% | toluene | 30 | 81 | >20:1 |
8 | L2 | 5 mol% | toluene | 30 | 20 | >20:1 |
9 | L3 | 5 mol% | toluene | 30 | trace | — |
10 | BINAP | 8 mol% | toluene | 30 | NR | — |
11 | BINAP | 5 mol% | toluene | 30 | 96 | >1:20 |
12 | BINAP | 4.7 mol% | toluene | 30 | 96 | >1:20 |
13 | BINAP | 2.5 mol% | toluene | 30 | 90 | 1:9 |
14 | BINAP | 5 mol% | DMA | 30 | trace | — |
15 | BINAP | 5 mol% | MeOtBu | 30 | 59 | >1:20 |
16 | BINAP | 5 mol% | dioxane | 30 | 95 | >1:20 |
17 | BINAP | 5 mol% | DCE | 30 | NR | — |
18 | BINAP | 5 mol% | THF | 30 | <5 | — |
19 | BINAP | 5 mol% | EtOH | 30 | NR | — |
20 | BINAP | 5 mol% | toluene | 0 | NR | — |
21c | BINAP | 5 mol% | toluene | 30 | 60 | >1:20 |
22c | PPh3 | 5 mol% | toluene | 30 | 81 | >20:1 |
