1067223-07-7Relevant academic research and scientific papers
Copper-hydroperoxo-mediated N-debenzylation chemistry mimicking aspects of copper monooxygenases
Maiti, Debabrata,Narducci Sarjeant, Amy A.,Karlin, Kenneth D.
, p. 8736 - 8747 (2008)
A substantial oxidative N-debenzylation reaction along with PhCH=O formation occurs from a hydroperoxo-copper(II) complex that has a dibenzylamino substrate (-N(CH2Ph)2 appended as a substituent on one pyridyl group of its tripodal tetradentate TMPA (also TPA, (2-pyridylmethyl) amine)) ligand framework. During the course of the (LN(CH2Ph)2)CuII(- QOH) reactivity, the formation of a substrate and a -OOH-derived (an oxygen atom) alkoxo CuII(-OR) complex occurs. The observation that the same CuII(-OR) species occurs from CuI/PhlO chemistry suggests the possibility that a copper-oxo (cupryl) reactive intermediate forms during the alkoxo species formation; new ESI-MS data provide further support for this high-valent intermediate. A net H atom abstraction chemistry is proposed on the basis of the kinetic isotope effect studies provided here and the previously published study for a closely related CuII(-OOH) species incorporating dimethylamine (-N(CH3)2) as the internal substrate;27 the CuI/PhlO reactivity with similar isotope effect results provides further support. The reactivity of these chemical systems closely resembles the proposed oxidative N-dealkylation mechanisms that are effected by the copper monooxygenases, dopamine β-monooxygenase (DβM) and peptidylglycine-α-hydroxylating monooxygenase (PHM).
