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. 2024 Feb 9;6(6):1648–1652. doi: 10.1039/d4na00075g

Photocatalytic aerobic oxidative hydroxylation of 4-methoxyphenylboronic acida.

graphic file with name d4na00075g-u2.jpg
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

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.

b

In mol L−1.

c

C. E. = control experiments.

d

Conversions determined from analysis of crude 1H NMR spectra.

e

Isolated yield after flash chromatography.

f

MLG was used instead of MLG-Ru.

g

MLG-1d was used instead of MLG-Ru.

h

Recovered MLG-Ru from entry 5 was reused in a new reaction.