Photoreductive Removal of O-Benzyl Groups from Oxyarene N-Heterocycles Assisted by O-Pyridine-pyridone Tautomerism
Facile photoreductive protocols have been developed to remove benzyl O-protective groups from oxyarene N-heterocycles at positions capable for 2-/4-O-pyridine-2-/4-pyridone tautomerism. Blue light irradiation, a [Ru] or [Ir] photocatalyst, and ascorbic acid in a water-acetonitrile solution debenzylates a variety of aryl N-heterocycles cleanly and selectively. Ascorbic acid has two functions in the reaction. On the one hand, it protonates the N-heterocycles that reduces their reduction potentials notably and on the other hand it acts as a sacrificial reductant. Reduction potentials and free energy barriers calculated at the CPCM-B3LYP/6-31+G? level can predict the reactivities of the studied substrates.
Todorov, Aleksandar R.,Wirtanen, Tom,Helaja, Juho
p. 13756 - 13767
(2017/12/26)
Tautomeric switching and metal-cation sensing of ligand-equipped 4-hydroxy-/4-oxo-1,4-dihydroquinolines
Novel 4-hydroxyquinoline (4HQ) based tautomeric switches are reported. 4HQs equipped with coordinative side arms (8-arylimino and 3-piperidin-1-ylmethyl groups) were synthesized to access O- or N-selective chelation of Zn 2+ and Cd2+
Todorov, Aleksandar R.,Nieger, Martin,Helaja, Juho
supporting information; experimental part
p. 7269 - 7277
(2012/07/27)
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