Abstract
High-power UV-LED irradiation (365 nm) effectively accelerated the decatungstate-anion-catalyzed oxidation of benzyl alcohol 1 to benzoic acid 3 via benzaldehyde 2. As the power of the UV-LED light increased, both the selectivity and yield of benzoic acid also increased. The reaction was finished within 1 h to give 3 in a 93% yield using 2 mol% of decatungstate anion catalyst. The combination of a flow photoreactor and high-power irradiation accelerated the oxidation reaction to an interval of only a few minutes.
Highlights
Decatungstate anion (W10 O32 4− ), when photo-excited, catalyzes C(sp3 )-H functionalization via hydrogen atom transfer (HAT) to create alkyl radicals [1,2,3,4,5]
When molecular oxygen or oxidizing reagents are present, decatungstate catalyzes the oxidation of C(sp3 )-H
We focused on catalytic oxidation using a decatungstate anion and molecular oxygen [21,22,23,24,25] under varied photo-irradiation conditions
Summary
Decatungstate anion (W10 O32 4− ), when photo-excited, catalyzes C(sp3 )-H functionalization via hydrogen atom transfer (HAT) to create alkyl radicals [1,2,3,4,5]. That situation motivated us to investigate how the decatungstate-anion-catalyzed oxidation would be affected when powered by photo-irradiation equipment. We focused on catalytic oxidation using a decatungstate anion and molecular oxygen [21,22,23,24,25] under varied photo-irradiation conditions. Scheme 1 illustrates the model oxidation reaction of 1, which leads to benzoic acid 3 via benzaldehyde 2, as well as the proposed mechanism. In this reaction, hydrogen atom transfer (HAT) by photo-excited decatungstate ion triggers the oxidation. Improving the catalytic efficiency of decatungstate-anion-catalyzed oxidation using molecular oxygen via high-power UV-LED
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