Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 6, Pages 4386-4397Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00102
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Funding
- National Natural Science Foundation of China [21922109, 21672196, 21602001, 21831007]
- Fundamental Research Funds for the Central Universities of China [WK2060190086]
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Salicylaldehyde is established as an efficient visible light photocatalyst for the first time. Compared to other simple aldehyde analogies, salicylaldehyde has a unique deprotonative red-shift from 324 to 417 nm and gives rise to the remarkable increase of fluorescence quantum from 0.0368 to 0.4632, thus enabling salicylaldehyde as a visible light (>400 nm) photocatalyst. The experimental investigations suggest that the reactive radical species are generated by sensitization of the substrates by the deprotonated salicylaldehyde through an energy-transfer pathway. Consequently, the C-C cleaving alkylation reactions of N-hydroxyphthalimide esters proceed smoothly in the presence of as low as 1 mol % of salicylaldehyde under the visible-light irradiation, affording desired alkylation products with up to 99% yields. Application in visible-light induced aerobic oxidation of N-alkylpyridinium salts is also reported.
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