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Visible Light-Induced Hydroxyalkylation of 1,2,4-Triazine-3,5(2H,4H)-dione with Alcohols via Oxidative
Xiaotong Fu1, Ranran Feng1, Yushi Tan1
1School of Chemical Engineering and Technology, Hebei Provincial Key Lab of Green Chemical Technology & High Efficient Energy Saving, Tianjin Key Laboratory of Chemical Process Safety, Hebei University of Technology, Tianjin 300130, P. R. China.
Abstract:
An unprecedented C6-H hydroxyalkylation of 1,2,4-triazine-3,5(2H,4H)-dione was achieved using readily available and inexpensive alcohols as the coupling partner, low-toxicity 2-tert-butylanthraquinone as the photocatalyst, sodium bicarbonate as the base, and air as the green oxidant via oxidative cross-dehydrogenative-coupling. The reaction conditions are mildly carried out under visible-light induction with good functional group tolerance and a wide substrate scope. A series of mechanistic exploration experiments demonstrated that the reaction proceeds via a radical mechanism. In addition, gram-scale experiments and application studies indicated that this method has a bright practical prospect.
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