Hydrogen Peroxide-Urea

Heaney, H.; Cardona, Francesca; Goti, Andrea; Frederick, Andrea L.

doi:10.1002/047084289x.rh047.pub3

Cited by 2 publications

(1 citation statement)

References 97 publications

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“…An ideal oxidative synthesis of N , N -dialkylhydroxylamines would give a high yield, have broad functional group tolerance, produce little to no overoxidation, and require only a simple purification method that results in products with high purity. Toward such a goal, UHP appeared to be an ideal source of anhydrous hydrogen peroxide, even if the reaction was slow in most standard solvents. Interestingly, fluorinated alcohol solvents, including 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP), have been shown to dramatically increase the rate of several types of oxidations using hydrogen peroxide .…”

Section: Resultsmentioning

confidence: 99%

Oxidative Syntheses of N,N-Dialkylhydroxylamines

Barriault,

Ly,

Allen

et al. 2024

J. Org. Chem.

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Despite the wide utility of hydroxylamines in organic synthesis, relatively few are commercially available, and there is a need for direct, efficient, and selective methods for their synthesis. Herein, we report two complementary methods to accomplish direct oxidation of secondary amines using UHP as an oxidant. The first method uses 2,2,2-trifluoroethanol (TFE) and a large excess of amine. Isolation of hydroxylamine products is enabled by selective salt formation, and recovery of excess amine is demonstrated. The second method uses hexafluoroacetone as an additive and is highlighted by the 1:1 stoichiometry between the oxidant and amine.

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Section: Resultsmentioning

confidence: 99%

Oxidative Syntheses of N,N-Dialkylhydroxylamines

Barriault,

Ly,

Allen

et al. 2024

J. Org. Chem.

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Dehydrogenase‐Catalyzed Oxidation of Furanics: Exploitation of Hemoglobin Catalytic Promiscuity

Jia

Zong

et al. 2017

ChemSusChem

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The catalytic promiscuity of hemoglobin (Hb) was explored for regenerating oxidized nicotinamide cofactors [NAD(P) ]. With H O as oxidant, Hb efficiently oxidized NAD(P)H into NAD(P) within 30 min. The new NAD(P) regeneration system was coupled with horse liver alcohol dehydrogenase (HLADH) for the oxidation of bio-based furanics such as furfural and 5-hydroxymethylfurfural (HMF). The target acids (e.g., 2,5-furandicarboxylic acid, FDCA) were prepared with moderate-to-good yields. The enzymatic regeneration method was applied in l-glutamic dehydrogenase (DH)-mediated oxidative deamination of lglutamate and for l-lactic-DH-mediated oxidation of l-lactate, which furnished α-ketoglutarate and pyruvate in yields of 97 % and 81 %, respectively. A total turnover number (TTON) of up to approximately 5000 for cofactor and an E factor of less than 110 were obtained in the bi-enzymatic cascade synthesis of α-ketoglutarate. Overall, a proof-of-concept based on catalytic promiscuity of Hb was provided for in situ regeneration of NAD(P) in DH-catalyzed oxidation reactions.

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Hydrogen Peroxide-Urea

Cited by 2 publications

References 97 publications

Oxidative Syntheses of N,N-Dialkylhydroxylamines

Oxidative Syntheses of N,N-Dialkylhydroxylamines

Dehydrogenase‐Catalyzed Oxidation of Furanics: Exploitation of Hemoglobin Catalytic Promiscuity

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