Journal
ORGANIC LETTERS
Volume 22, Issue 13, Pages 5207-5211Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01852
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Funding
- Nanotechnology Platform Program (Molecule and Material Synthesis) of the Ministry of Education Culture, Sports, Science and Technology (MEXT), Japan
- Yokohama National University
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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 beta-bromostyrene (E-p/2 = +1.61 V vs SCE) were selectively oxidized by a thioxanthylium photoredox catalyst (E-1/2 (C*/C center dot-) = +1.76 V vs SCE) to styryl radical cations and reacted with styrene (E-p/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 beta-halogenostyrenes, which cannot be effectively achieved by the hitherto reported representative organophotoredox catalysts.
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