Journal
TETRAHEDRON
Volume 74, Issue 20, Pages 2421-2427Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.03.040
Keywords
Heterogeneous photocatalysis; Oxygenation; Selective oxidation; Solar synthesis; Cascade reaction
Categories
Funding
- NSFC [21401117]
- Natural Science Foundation of Shandong Province [ZR2014BQ003]
- Shandong University [104.205.2.5]
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We report the selective formation of endoperoxides by aerobic TiO2 photocatalysis through the cyclic addition of dioxygen and a non-conjugated diene, the first heterogeneous catalytic system for endoperoxide synthesis. This green protocol does not require any additive and the photocatalyst is abundant and recyclable, providing a yield up to 64% and >20:1 diastereoselectivity. Mechanistic investigations were carried out by using product analysis, kinetic studies, O-18 labelling experiments, electron-spin resonance and a set of quenching experiments. Superoxide (but not singlet oxygen, triplet oxygen or peroxide) is directly involved in the reaction cascade to form the endoperoxide product The new findings may be helpful for future for designing eco-friendly and energy sustainable strategies for selective oxygenation reactions using semiconductors, O-2 and sunlight. (C) 2018 Elsevier Ltd. All rights reserved.
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