Photocatalytic aerobic oxidative hydroxylation of 4-methoxyphenylboronic acida.
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|---|---|---|---|---|---|---|
| Ent. | DMF | [5]b | t (h) | C. E.c | 6d (%) | 6e (%) |
| 1 | 0.1 mL | 0.70 | 36 | — | nr | — |
| 2 | 0.5 mL | 0.14 | 36 | — | nr | — |
| 3 | 1.0 mL | 0.07 | 36 | — | 45 | 40 |
| 4 | 1.5 mL | 0.04 | 36 | — | 48 | 41 |
| 5 | 1.0 mL | 0.07 | 72 | — | 94 | 88 |
| 6 | 1.0 mL | 0.07 | 72 | MLGf | nr | — |
| 7 | 1.0 mL | 0.07 | 72 | MLG1dg | nr | — |
| 8 | 1.0 mL | 0.07 | 72 | No MLG-Ru | nr | — |
| 9 | 1.0 mL | 0.07 | 72 | Inert atm. | nr | — |
| 10 | 1.0 mL | 0.07 | 72 | No DIPEA | nr | — |
| 11 | 1.0 mL | 0.07 | 72 | Blue light | nr | — |
| 12 | 1.0 mL | 0.07 | 72 | Darkness | nr | — |
| 13 | 1.0 mLh | 0.07 | 72 | — | 95 | 88 |
A mass of 20 mg of MLG-Ru, in DMF, 5 (0.07 mmol), DIPEA (0.14 mmol), white LED light (14 W), and air atmosphere at room temperature. nr = no reaction.
In mol L−1.
C. E. = control experiments.
Conversions determined from analysis of crude 1H NMR spectra.
Isolated yield after flash chromatography.
MLG was used instead of MLG-Ru.
MLG-1d was used instead of MLG-Ru.
Recovered MLG-Ru from entry 5 was reused in a new reaction.