Product Class 5: Hydroxylamines

Enders,; Schaumann,

doi:10.1055/sos-sd-040-00666

Cited by 2 publications

(2 citation statements)

References 512 publications

(820 reference statements)

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“…Hydroxylamines can also directly undergo hydroamination with alkenes or alkynes via Cope-type hydroamination, forming hydroxylamine, N -oxide, oxime, or nitrone products . However, the broader use of hydroxylamines is hindered by their inefficient syntheses . In particular, unsymmetrical secondary hydroxylamines often require indirect syntheses, most often achieved by oxidation of a primary amine followed by alkylation. , In this context, methods based on the oxidation of amines are attractive and can provide access to secondary hydroxylamines in fewer steps.…”

Section: Introductionmentioning

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: Introductionmentioning

confidence: 99%

Oxidative Syntheses of N,N-Dialkylhydroxylamines

Barriault,

Ly,

Allen

et al. 2024

J. Org. Chem.

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“…Due to their high nucleophilicity, chemical architectures decorated with this functionality have widely been applied in diverse chemical synthesis, bioconjugation strategies, and protocols for amide bond formation . Among the established strategies for their preparation, the selective addition of nucleophilic species to nitrones represents a straightforward way for accessing N , N -disubstituted hydroxylamines . These protocols mainly involve the use of Grignard and organozinc reagents, enolates, cyanide, acyl, and carbamoyl anions .…”

Section: Introductionmentioning

confidence: 99%

Visible-Light Mediated Carbamoylation of Nitrones under a Continuous Flow Regime

et al. 2022

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Herein, we report a rapid and scalable continuousflow photocatalytic approach for the carbamoylation of nitrones. This protocol makes use of readily available 4-amido-1,4 dihydropyridines as carbamoyl radical precursors. The scope of this transformation exhibits high compatibility with complex structures containing amino acids, peptides, and glycosides. Importantly, the developed method allows a photocatalytic synthetic strategy in combination with flow conditions, maximizing the potential and efficiency for the synthesis of valuable α-(Nhydroxy)amino amides.

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Product Class 5: Hydroxylamines

Cited by 2 publications

References 512 publications

Oxidative Syntheses of N,N-Dialkylhydroxylamines

Oxidative Syntheses of N,N-Dialkylhydroxylamines

Visible-Light Mediated Carbamoylation of Nitrones under a Continuous Flow Regime

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