Table 1.
Optimization of gold-catalyzed oxo-arylfluorinationa
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Entry | Variation of standard conditions | Yield(%)b |
1 | None | 70 |
2 | Ph3PAuCl (10 mol%) | 58 |
3 | dppm(AuCl)2 (5 mol%) | 38 |
4 | (4-CF3Ph)3PAuTFA (10 mol%) | 53 |
5 | (4-CF3Ph)3PAuOTs (10 mol%) | 50 |
6 | without (4-CF3Ph)3PAuCl | N.D. |
7 | H2O (5.0 equiv) | 61 |
8 | without H2O | 49 |
9 | NFSI instead of Selectfluor | N.D. |
aStandard reaction conditions: 1a (0.1 mmol), 2a (0.3 mmol), (4-CF3Ph)3PAuCl (10 mol%), Selectflour (4.0 equiv.), H2O (2.0 equiv.), MeCN (2.0 mL), 50 °C, air, 12 h.
bIsolated yields. dppm bis(diphenylphosphino)methane, Selectfluor 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), NFSI N-fluorobenzenesulfonimide.