TiO2 Photocatalytic Cyclization Reactions for the Syntheses of Aryltetralones

This work focuses on a new strategy to overcome the overoxidation in heterogeneous TiO2 photocatalysis and to realize high-efficiency photosynthesis. We demonstrate that TiO2 photocatalysis can integrate C–C and CO formation in a tandem manner to achieve efficient oxidative cyclization for the synt...

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Veröffentlicht in:ACS catalysis 2016-12, Vol.6 (12), p.8389-8394
Hauptverfasser: Liu, Yuliang, Zhang, Mingfu, Tung, Chen-Ho, Wang, Yifeng
Format: Artikel
Sprache:eng
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Zusammenfassung:This work focuses on a new strategy to overcome the overoxidation in heterogeneous TiO2 photocatalysis and to realize high-efficiency photosynthesis. We demonstrate that TiO2 photocatalysis can integrate C–C and CO formation in a tandem manner to achieve efficient oxidative cyclization for the syntheses of aryltetralones. This protocol does not need any additive besides the inexpensive and/or recyclable TiO2, O2, and (solar) light. High yields with excellent diastereoselectivities are obtained for a wide scope of electron-rich substrates. Our findings demonstrate that in contrast to the conventional overoxidation, as long as the radical cations possess sufficient reactivity toward nucleophilic addition, single-electron transfer processes in TiO2 photocatalysis can be developed into a powerful tool to construct C–C bonds and even strained carbon rings.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.6b03076