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Updated: Dec 18, 2025
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Redox Potential Controlled Selective Oxidation of Styrenes for Regio- and Stereoselective Crossed Intermolecular [2 +
Kenta Tanaka1, Yoshinori Iwama2, Mami Kishimoto2
1Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
Abstract:
A redox potential controlled intermolecular [2 + 2] cross-cycloaddition has been developed in the presence of a thioxanthylium photoredox catalyst. Electron-rich styrenes such as β-bromostyrene (Ep/2 = +1.61 V vs SCE) were selectively oxidized by a thioxanthylium photoredox catalyst (E1/2 (C*/C•-) = +1.76 V vs SCE) to styryl radical cations and reacted with styrene (Ep/2 = +1.97 V vs SCE) to furnish polysubstituted cyclobutanes in high yields. The present reaction can be successfully applied to intermolecular [2 + 2] cross-cycloaddition of β-halogenostyrenes, which cannot be effectively achieved by the hitherto reported representative organophotoredox catalysts.
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