Table 1 Effect of reaction parameters.
From: Enantioselective alkylative cross-coupling of unactivated aromatic C–O electrophiles
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|---|---|---|---|
Entry | Variation from standard conditions | Yield (%) | ee (%) |
1 | none | 96(97) | 98 |
2 | no Ni(cod)2 | 0 | n.d. |
3 | no L1 | <5 | n.d. |
4 | NiBr2(dme) instead of Ni(cod)2 | 97 | 97 |
5 | NiBr2 instead of Ni(cod)2 | 18 | 78 |
6 | L2-L8 instead of L1 | listed as below | |
7 | THF instead of PhMe | 68 | 91 |
8 | DCM instead of PhMe | <5 | n.d. |
9 | 1,4-dioxane instead of PhMe | 9 | 58 |
10 | DME instead of PhMe | 56 | 72 |
11 | 45 °C instead of 60 °C | 95 | 98 |
12 | 80 °C instead of 60 °C | 96 | 95 |
13 | Ni(cod)2 (10 mol%), L1 (12 mol%) | 96 | 94 |
14 | Ni(cod)2 (5 mol%), L1 (10 mol%) | 95 | 94 |
15 | Ni(cod)2 (1 mol%), L1 (2 mol%) | <5 | n.d. |
16 | Me-MgI instead of Me-MgBr | 25 | 94 |
17 | Me-MgCl instead of Me-MgBr | 95 | 70 |
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