jo0c00102_si_001.pdf (3.24 MB)
Deprotonated Salicylaldehyde as Visible Light Photocatalyst
journal contribution
posted on 2020-02-25, 19:47 authored by Yan-Jun Zhuang, Jian-Ping Qu, Yan-Biao KangSalicylaldehyde 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.