21 research outputs found
Photocatalytic Strategy to Realize N‑Debenzylation via Aerobic Oxidation Catalyzed by 4CzIPN
It is a great challenge to remove the N-benzyl
protecting group selectively by photocatalytic aerobic oxidation because
amides or imines are easily formed from the oxidation of N-benzylamine. In this study, a visible-light-induced debenzylation
in yields of up to 88% was realized with a low catalytic loading of
an organophotocatalyst [2 mol % 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene
(4CzIPN)] in the presence of air and HCl under mild conditions. Mechanisms
involving two-electron-transfer processes, a proton-transfer process,
and a hydrolysis process were proposed based on the experimental studies
and density functional theory (DFT) calculations. Acetone plays an
important role in the proton-transfer process to promote these debenzylations