Synthesis of imines from nitrobenzene and TiO2 particles suspended in alcohols via semiconductor photocatalysis type B

(Green) Photocatalytic Synthesis Employing Nitroaromatic Compounds

“…Since bare TiO 2 is hardly able to reduce protons [15] the formation of N-alkylarylamines 7 is not observed in the absence of noble metal deposits. This finding is in agreement with experimental results published by Valenzuela and coworkers who have found imines 3 as the sole C-N-coupling product between photocatalytically formed aniline and ethanal in bare TiO 2 suspensions [9]. When Au@TiO 2 is used as the photocatalyst imines 3 are also found to be the main products under the experimental conditions of this work.…”

“…Ar-NO 2 + 6 H + + 6 TiO 2 {e -} → Ar-NH 2 + 2 H 2 O + 6 TiO 2 (1) While imines 3 were found as the sole C-N-coupling products during the photocatalytic reactions of nitrobenzene and alcohols in the presence of bare TiO 2 [9] it is supposed that the aniline, Ar-NH 2 , reacts with ethanal, CH 3 -CHO, yielding an imine in a subsequent thermal reaction (reaction 3).…”

“…1,3-Dimethyl-1H-indole, 2,3-dimethyl-1H-indole, 2-methylquinoline, 2-methyl-quinoline-1-oxide, and 3-methylquinoline-2(1H)-one, probably formed via reactions between aniline and the products of the photocatalytic ethanol oxidation, were identified by GC-MS [8]. Valenzuela and co-workers have also demonstrated the synthesis of imines from nitrobenzene and alcohols (primary C1 -C5 alcohols, and 2-propanol) in the presence of UV(A) irradiated TiO 2 [9].…”

Heterogeneous photocatalytic organic synthesis: state-of-the-art and future perspectives

“…Higher alcohols led to the formation of a mixture of aniline and imines. 91 Hakki et al 87 showed that the selectivity of this reaction is also dependent on the surface properties of the employed TiO 2 photocatalyst where the surface Lewis acidity plays an important role. Anatase has a much higher Lewis acidity than rutile, which promoted imine selectivity.…”

Identification of Structural Features of 2‐Alkylidene‐1,3‐Dicarbonyl Derivatives that Induce Inhibition and/or Activation of Histone Acetyltransferases KAT3B/p300 and KAT2B/PCAF

“…In addition, 4‐methylbenzyl alcohol ( 1 b ), 4‐chlorobenzyl alcohol ( 1 c ), and 4‐bromobenzyl alcohol ( 1 c ) could also be utilized in the present system (Table 2, entries 4–6). Remarkably, the present photocatalytic system was applicable to nitroarenes possessing additional reducible groups such as the CC bond (Table 2, entry 10), CC bond (Table 2, entry 11), Cl (Table 2, entry 12), and CO (Table 2, entries 13 and 14); nitro groups were selectively reduced to the amino groups and the corresponding N ‐arylimines were successfully obtained 20…”