Table 1.
Development of the vanadium-catalyzed C—H fluorination reactiona
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---|---|---|---|---|
Entry | Catalyst loading | Catalyst | Fluorine source | Yieldb |
1 | 10 mol % | V2O5 | A | 0% |
2 | 20 mol % | VO(OiPr)3 | A | 0% |
3 | 20 mol % | VO(OSiPh3)3 | A | 0% |
4 | 20 mol % | VOF3 | A | 0% |
5 | 20 mol % | V(O)SO4 | A | 0% |
6 | 20 mol % | VO2 | A | <5% |
7 | 20 mol % | Cp2VCl2 | A | <5% |
8 | 20 mol % | VF3 | A | <5% |
9 | 20 mol % | VBr3 | A | <5% |
10 | 20 mol % | V(acac)3 | A | 21% |
11 | 10 mol % | V2O3 | A | 73% (65%)c |
12 | 20 mol % | Cp2V | A | 13% |
13 | 10 mol % | V2O3 | B | 0% |
14 | 10 mol % | V2O3 | C | 0% |
15 | 10 mol % | V2O3 | D | 0% |
16 | 10 mol % | – | A | 0% |
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Conditions: 1 (0.2 mmol), catalyst (0.04 mmol, or 0.02 mmol for V2O5 and V2O3), Selectfluor (0.3 mmol), CH3CN (2 mL), 23 °C.
Based on crude 19F NMR spectra using C6H5F as the external standard.
Isolated yield in parenthesis.