Facile Aerobic Photooxidation of Alcohols Using 2-Chloroanthraquinone under Visible Light Irradiation

Shimada, Yoshiko; Hattori, Kasumi; Tada, Norio; Miura, Tsuyoshi; Itoh, Akichika

doi:10.1055/s-0033-1338420

Cited by 28 publications

(7 citation statements)

References 1 publication

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“…Based on the results described above, as well as those previously reported, [46,48] the mechanism proposed for the oxidative hydroxylation of arylboronic acids is that depicted in Figure 4. At first, the heterogeneous SNPs−AQ PC is excited under visible‐light irradiation to generate SNPs−AQ*, which abstracts a hydrogen atom from 2‐PrOH to produce 2‐isopropanol radical ( 3 ) and reduced SNPs−AQH⋅ [49] .…”

Section: Resultssupporting

confidence: 66%

“…The negligible amount of AQÀ COOH released from SNPs during the reaction progress could be responsible for the small amount of phenol 2 a produced after the filtration (< 10 %). Based on the results described above, as well as those previously reported, [46,48] the mechanism proposed for the oxidative hydroxylation of arylboronic acids is that depicted in Figure 4. At first, the heterogeneous SNPsÀ AQ PC is excited under visible-light irradiation to generate SNPsÀ AQ*, which abstracts a hydrogen atom from 2-PrOH to produce 2isopropanol radical (3) and reduced SNPsÀ AQH * .…”

Section: Evaluation Of Photocatalytic Activitysupporting

confidence: 68%

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Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids

Guadalupe Martin,

Lázaro‐Martínez,

Martín

et al. 2024

Chemistry A European J

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In this work, the synthesis and characterization of a heterogeneous photocatalyst based on spherical silica nanoparticles superficially modified with anthraquinone 2‐carboxylic acid (AQ‐COOH) are presented. The nanomaterial was characterized by TEM, SEM, FT‐IR, diffuse reflectance, fluorescence, NMR, DLS, XRD and XPS. These analyses confirm the covalent linking of AQ‐COOH with the NH2 functionality in the nanomaterial and, more importantly, the photocatalyst retains its photophysical properties once bound. The heterogeneous photocatalyst was successfully employed in the aerobic hydroxylation of arylboronic acids to phenols under sustainable reaction conditions. Phenols were obtained in high yields (up to 100 %) with low catalyst loading (3.5 mol %), reaching TOF values of 3.7 h‐1. Using 2‐propanol as solvent at room temperature, the visible light photocatalysis produced H2O2 as a key intermediate to promote the aerobic hydroxylation of arylboronic acids. The heterogeneous photocatalyst was reused at least 5 times, without modification of the nanomaterial structure and morphology. This simple heterogeneous system showed great catalytic activity under sustainable reaction conditions.

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Section: Resultssupporting

confidence: 66%

Section: Evaluation Of Photocatalytic Activitysupporting

confidence: 68%

Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids

Guadalupe Martin,

Lázaro‐Martínez,

Martín

et al. 2024

Chemistry A European J

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show abstract

“…The negligible amount of AQ-COOH released from SNPs during the reaction progress could be responsible for the small amount of phenol 2a produced after the filtration (< 10 %). Based on the results described above, as well as those previously reported, [46], [48] the mechanism proposed for the oxidative hydroxylation of arylboronic acids is that depicted in Figure 4. At first, the heterogeneous SNPs-AQ PC is excited under visible-light irradiation to generate SNPs-AQ*, which abstracts a hydrogen atom from 2-PrOH to produce 2-isopropanol radical (3) and reduced SNPs-AQH .…”

Section: Evaluation Of Photocatalytic Activitysupporting

confidence: 68%

Anthraquinone-Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids

Martín¹,

Martín²,

Uberman³

et al. 2023

Preprint

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“…A less explored but promising approach that can complement the AO process is to use the excited-state properties of anthraquinones (or other chromophores) − to catalyze the production of H 2 O 2 from air. Anthraquinones are highly useful in organic photoredox catalysis, , having been used to initiate the photooxidation of benzylic substituents, , 1,3-diketones, alcohols, and to epoxidize enones . They have also successfully been employed in arene hydrodehalogenations .…”

Section: Introductionmentioning

confidence: 99%

On-Demand Photochemical Synthesis of Hydrogen Peroxide from Alkylated Anthraquinones

Vibbert

Bendel

Norton

et al. 2022

ACS Sustainable Chem. Eng.

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Direct illumination of anthraquinones with light, in air, to produce H 2 O 2 reliably and robustly has been developed for aqueous, electrolyte-free, highly pure H 2 O 2 production. Effects of chromophore, solvent, air saturation, and light source have been investigated to understand the mechanism of this transformation. Upon photosensitization of an air-saturated, biphasic solution consisting of an organic solvent and water, H 2 O 2 can be quickly and linearly produced with the oxidized solvent remaining in the organic phase. The mechanism of this transformation has been probed using computational methods, suggesting that proton-coupled electron transfer from an organic solvent to an anthraquinone catalyst is the most likely mechanistic pathway. Commercially relevant H 2 O 2 concentrations, as high as 2.34% (w/w), have been produced in 3 h, among the fastest photochemical H 2 O 2 production reaction reported.

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Facile Aerobic Photooxidation of Alcohols Using 2-Chloroanthraquinone under Visible Light Irradiation

Cited by 28 publications

References 1 publication

Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids

Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids

Anthraquinone-Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids

On-Demand Photochemical Synthesis of Hydrogen Peroxide from Alkylated Anthraquinones

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