Chemoselective hydrogen peroxide oxidation of primary alcohols to aldehydes by a water-soluble and reusable iron(<scp>iii</scp>) catalyst in pure water at room temperature

Yan, Qi; Fang, Ye Chen; Jia, Yun; Duan, Xin Hong

doi:10.1039/c6nj03793c

Cited by 26 publications

(5 citation statements)

References 72 publications

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“…Electron paramagnetic resonance spectra were obtained on a Bruker EPR spectrometer. Ligand L1 , N -methylquinolin-8-amine, 2-(chloromethyl)-1 H -benzo[ d ]imidazole, Mn5 , and Mn6 were prepared following previous literature report.…”

Section: Methodsmentioning

confidence: 99%

Well-Defined Phosphine-Free Manganese(II)-Complex-Catalyzed Synthesis of Quinolines, Pyrroles, and Pyridines

et al. 2022

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Herein, we report a simple, phosphine-free, and inexpensive catalytic system based on a manganese(II) complex for synthesizing different important N-heterocycles such as quinolines, pyrroles, and pyridines from amino alcohols and ketones. Several control experiments, kinetic studies, and DFT calculations were carried out to support the plausible reaction mechanism. We also detected two potential intermediates in the catalytic cycle using ESI-MS analysis. Based on these studies, a metal–ligand cooperative mechanism was proposed.

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Section: Methodsmentioning

confidence: 99%

Well-Defined Phosphine-Free Manganese(II)-Complex-Catalyzed Synthesis of Quinolines, Pyrroles, and Pyridines

et al. 2022

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“…Utilizing H 2 O 2 , the authors demonstrated that aromatic alcohols were oxidized in lower yields due to competing aryl hydroxylation reactions. Duan reported chemoselective oxidation of primary alcohols to aldehydes by a water‐soluble and reusable iron(III) catalyst utilizing H 2 O 2 as the oxidant under aqueous conditions (entry 12) . The catalyst system was generated in situ from FeCl 3 and an ammonium salt‐functionalized 8‐aminoquinoline 10 .…”

Section: Oxidation Of Alcoholsmentioning

confidence: 99%

Recent Advances in Iron Catalyzed Oxidation Reactions of Organic Compounds

Bauer

2017

Israel Journal of Chemistry

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Iron-catalyzed oxidation reactions have been increasingly investigated in the past two decades and have seen a major increase in research activity. This review article demonstrates the vigorous research activities in the field based on examples from the most recent literature. Catalyst systems are discussed that are active in the oxygenation of alkanes and alkenes to obtain alcohols, ketones or epoxides. Iron-catalyzed oxidation of alcohols to the corresponding carbonyl units are also included. Enantioselective and heterogeneous catalyst systems are presented as well, and a brief overview of mechanistic pictures is given. B. Bauer was born in Nuremberg, Germany. He received PhD degree in 2003 from the University of Erlangen-Nuremberg; under the supervision of Prof. John A. Gladysz, he performed ring closing metathesis reactions in the coordination sphere of transition metals to obtain macrocyclic metal complexes. He performed postdoctoral research at the University of California, Riverside with Keith Hollis, working on rhodium and iridium carbene complexes with catalytic activity in hydroamination and hydrosilylation reactions. In 2005 he joined Illinois Wesleyan University for one year as a Visiting Assistant Professor. In 2006 he joined the University of Missouri -St. Louis as an Assistant Professor, and became promoted to Associate Professor in 2012. His research interests are the synthesis and characterization of ruthenium and iron complexes to be employed in catalytic processes. His work on ruthenium mainly concerns the catalytic activation of propargylic alcohols and their derivatives toward nucleophilic substitution reactions. In the area of iron catalysis, he published a number of iron complexes to be catalytically active in the oxidation of hydrocarbons and alcohols.

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“…Additional references cited within the Supporting Information. [31][32][33][34][35][36][37][38][39][40][41]…”

Section: General Experimental Sectionmentioning

confidence: 99%

An In‐Situ‐Formed Copper‐Based Perfluorinated Catalytic System for the Aerobic Oxidation of Alcohols

Drymona,

Kaplanai,

Vougioukalakis

2024

Eur J Org Chem

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Herein, we report a new catalytic protocol for the aerobic oxidation of alcohols. The catalytic system is formed in situ, in a straightforward and user‐friendly manner, combining a widely available copper source (Cu2O) with one imidazolium salt precursor bearing perfluorinated moieties. Our protocol uses TEMPO, as additive, and the reaction takes place at the interface of a biphasic solvent system, consisting of anisole and 1‐bromoperfluorooctane. The as‐prepared carbonyl compounds remain in the organic solvent, while the catalytic system remains in the fluorous phase. In this manner, the isolation and purification of the desired products are quite facile. Our protocol uses low catalytic loadings and is more efficient with primary alcohols, affording the desired products in good to excellent yields. The fluorous phase containing the catalytic system can be efficiently recovered and reused for at least six times, without a significant decrease in its catalytic efficiency.

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Chemoselective hydrogen peroxide oxidation of primary alcohols to aldehydes by a water-soluble and reusable iron(iii) catalyst in pure water at room temperature

Abstract: A novel, water-soluble and reusable FeCl3 catalyst showed high catalytic activity and chemoselectivity in the H2O2-oxidation of primary alcohols into aldehydes.

Cited by 26 publications

References 72 publications

Well-Defined Phosphine-Free Manganese(II)-Complex-Catalyzed Synthesis of Quinolines, Pyrroles, and Pyridines

Well-Defined Phosphine-Free Manganese(II)-Complex-Catalyzed Synthesis of Quinolines, Pyrroles, and Pyridines

Recent Advances in Iron Catalyzed Oxidation Reactions of Organic Compounds

An In‐Situ‐Formed Copper‐Based Perfluorinated Catalytic System for the Aerobic Oxidation of Alcohols

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