Table 1.
Effect of Reaction Parameters on the Fluorination of Arylsilanes.[a]
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|---|---|---|---|---|
| Entry | [Cu] (equiv) | [F−] (equiv) | T [°C] | Yield (%)[b] |
| 1 | Cu(OTf)2 (3.0) | KHF2 (4.0) | 120 | trace |
| 2 | Cu(OTf)2 (3.0) | KHF2 (4.0) | 80 | 25 |
| 3 | Cu(OTf)2 (3.0) | KHF2 (4.0) | 65 | 40 |
| 4 | Cu(OTf)2 (3.0) | KHF2 (4.0) | 50 | trace |
| 5 | Cu(OTf)2 (2.0) | KHF2 (4.0) | 65 | trace |
| 6 | Cu(OTf)2 (6.0) | KHF2 (4.0) | 65 | 60 |
| 7 | Cu(OTf)2 (6.0) | KHF2 (6.0) | 65 | 74 |
| 8 | CuF2 (6.0) | KHF2 (6.0) | 65 | 0 |
| 9 | (tBuCN)CuOTf (6.0) | KHF2 (6.0) | 65 | 0 |
| 10 | Cu(OTf)2 (6.0) | AgF (6.0) | 65 | 0 |
| 11 | Cu(OTf)2 (6.0) | CsF (6.0) | 65 | 23 |
Reactions run on a 0.05 mmol scale.
Determined by 19F NMR spectroscopy with 1-fluoro-3-nitrobenzene as internal standard.
