Table 1 Deoxytrifluoromethylation/aromatization of activated substrates
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Entry | R | Conditions (Step 1) | Yield (19F NMR) | Conditions (Step 2) | Yield (19F NMR) |
1.1 | Ph | TMSCF3 (1.1 equiv.) 10% TBAF THF (0.5 M) rt, 4 h | 99% | – | – |
1.2 | Ph | – | – | PTSA•H2O (1 equiv.) DDQ (1 equiv.) o-xylene (0.1 M) 110 °C, 14 h | 5% |
1.3 | Ph | – | – | PTSA•H2O (1 equiv.) DDQ (3 equiv.) PhMe (0.2 M) 110 °C, 14 h | 70% |
1.4 | Ph | TMSCF3 (1.1 equiv.) 10% TBAF THF (0.5 M) rt, 4 h | 99% | PTSA•H2O (1 equiv.) DDQ (3 equiv.) THF (0.2 M) 65 °C, 14 h | 0% |
1.5 | Ph | TMSCF3 (1.1 equiv.) 10% TBAF PhMe (0.5 M) rt, 4 h | 92% | PTSA•H2O (1 equiv.) DDQ (3 equiv.) PhMe (0.2 M) 110 °C, 14 h | 4% |
1.6 | Ph | TMSCF3 (1.1 equiv.) 10% CsF PhMe (0.5 M) rt, 4 h | 99% | PTSA•H2O (1 equiv.) DDQ (3 equiv.) PhMe (0.2 M) 110 °C, 14 h | 14% |
1.7 | Ph | TMSCF3 (1.1 equiv.) 10% CsF o-DCB (0.5 M) rt, 4 h | 99% | PTSA•H2O (1 equiv.) DDQ (3 equiv.) o-DCB (0.2 M) 110 °C, 14 h | 62% |
1.8 (Conditions A) | Ph | TMSCF3 (1.1 equiv.) 10% CsF o-DCB (0.5 M) rt, 4 h | 99% | PTSA•H2O (2 equiv.) DDQ (3 equiv.) o-DCB (0.2 M) 140 °C, 14 h | 99% |
1.9 | tBu | TMSCF3 (1.1 equiv.) 10% CsF o-DCB (0.5 M) rt, 4 h | 99% | PTSA•H2O (2 equiv.) DDQ (3 equiv.) o-DCB (0.2 M) 140 °C, 14 h | 0% |
