Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 16, Pages 7217-7229Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01102
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Funding
- MEXT/JSPS KAKENHI [25460028, 23105007]
- Grants-in-Aid for Scientific Research [25460028, 16H06384, 15K07879] Funding Source: KAKEN
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The utility of rhodamine B as a water-soluble organic photocatalyst was studied in the cascade radical addition-cydization-trapping reactions under visible light irradiation. In the presence of (i-Pr)(2)NEt, the electron transfer from the excited rhodamine B to perfluoroalkyl iodides proceeded smoothly to promote the carbon-carbon bond-forming radical reactions in aqueous media. When i-C3F2I was employed as a radical precursor, the aqueous-medium radical reactions proceeded even in the absence of (i-Pr)(2)NEt. In these reactions, the direct electron transfer from the excited singlet state of rhodamine B would take place. Furthermore, the cleavage of the C-I bond in less reactive i-PrI could be achieved by the reductive electron transfer from the excited rhodamine B, which was confirmed by the fluorescence quenching of rhodamine B with the addition of i-PrI.
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