2007
DOI: 10.1021/ja071623g
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Aromatic Hydroxylation Reactivity of a Mononuclear Cu(II)−Alkylperoxo Complex

Abstract: The reactions of copper(II) complexes and hydrogen peroxide (H 2 O 2 ) have been studied extensively in order to gain insight into reactive intermediates involved in copper monooxygenases and copper oxidases as well as copper-catalyzed oxidation reactions. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] Several types of mononuclear and dinuclear copper/active-oxygen complexes have been reported, and their structures and physicochemical properties have been explored in detail. [1][2][3][4][5… Show more

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Cited by 50 publications
(88 citation statements)
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“…Based on the analogy of the resonance Raman features with those of reported Cu II -alkylperoxide complexes, [8][9][10][11] a similar type of alkylperoxide complex may be generated in the present reaction. Thus, the band at 831 cm -1 is assigned to the O-O stretching vibrations, whereas the band at 604 cm -1 is due to the Cu-O stretching vibration.…”
Section: Introductionmentioning
confidence: 79%
“…Based on the analogy of the resonance Raman features with those of reported Cu II -alkylperoxide complexes, [8][9][10][11] a similar type of alkylperoxide complex may be generated in the present reaction. Thus, the band at 831 cm -1 is assigned to the O-O stretching vibrations, whereas the band at 604 cm -1 is due to the Cu-O stretching vibration.…”
Section: Introductionmentioning
confidence: 79%
“…Thus, we consider C-H oxidation by a Cu(II)-oxyl ROS, dubbed the "oxyl mechanism" (Fig. 3) as this species has been previously predicted to exhibit a more strongly oxidative character than Cu(II)-superoxo (31,32 (20,33,34). From this system, we test two different geometries for oxidative attack at the C1 and C4 carbons to evaluate different enzyme-substrate poses (SI Appendix, Fig.…”
Section: Resultsmentioning
confidence: 99%
“…180,184 An acetone molecule is functionalized to yield the novel species 13 , the characterization of which is described below (section 2.2.2). The 2-hydroxy-2-peroxypropane ligand was formed in an analogous way upon reaction of an iron(II) complex with H 2 O 2 in acetone.…”
Section: Monocopper Compoundsmentioning
confidence: 99%