Photocatalytic Oxidation of Benzyl Alcohol by Homogeneous CuCl<sub>2</sub>/Solvent: A Model System to Explore the Role of Molecular Oxygen

Meng, Chao; Yang, Kai; Fu, Xianzhi; Yuan, Rusheng

doi:10.1021/acscatal.5b00644

Cited by 84 publications

(47 citation statements)

References 37 publications

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“…Although doubly labeled products were also observed, the unlabeled form was most likely generated by H/D exchange between the 18 O-labeled products and water. [12] The oxidative cleavage of indoles is a light-dependent process, as demonstrated by the experimental results shown in Figure 1. The yield of the model reaction under visible light increased over time, whereas there was no enhancement in the yield when the reaction mixture was stirred in the dark.…”

Section: Resultsmentioning

confidence: 91%

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Aerobic C–C Bond Cleavage of Indoles by Visible‐Light Photoredox Catalysis with Ru(bpy)₃²⁺

Wang

et al. 2017

Eur J Org Chem

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Photoredox catalysis with Ru(bpy)32+ (2,2′‐bipyridine) has been used to enable the activation of oxygen in the aerobic C–C cleavage/oxygenation reaction of indoles. A number of indole substrates that contain various functional groups were successfully employed in the reaction to give a wide range of ortho‐aminobenzaldehyde derivatives. These products can then be used as versatile building blocks for further synthetic modifications. Mechanistic studies suggest that the reaction proceeds through a radical pathway.

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Section: Resultsmentioning

confidence: 91%

“…In all of the cases, HRMS analysis revealed the major product to contain one 18 O atom. Although doubly labeled products were also observed, the unlabeled form was most likely generated by H/D exchange between the 18 O‐labeled products and water …”

Section: Resultsmentioning

confidence: 99%

Aerobic C–C Bond Cleavage of Indoles by Visible‐Light Photoredox Catalysis with Ru(bpy)₃²⁺

Wang

et al. 2017

Eur J Org Chem

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“…Low yields and poor selectivity have been the main drawbacks associated with catalytic oxidation reactions. Recently, the selective oxidation of benzyl alcohols to benzaldehyde by using iron oxide-based nanocomposites [17], ionic liquid-modified MIL-100(Fe) [18], developed copper(Ι)/TEMPO catalysts (TEMPO = 2,2,6,6-tetramethylpiperidinyl-N-oxyl) [19,20], photocatalytic oxidation by homogeneous CuCl2 [21], metal-free systems [22], photoactive VO@g-C3N4 [23] and Co oxide nanoparticles [24], among others have been reported.…”

Section: Introductionmentioning

confidence: 99%

Versatile Sulfathiazole-Functionalized Magnetic Nanoparticles as Catalyst in Oxidation and Alkylation Reactions

et al. 2019

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Catalyst design and surface modifications of magnetic nanoparticles have become attractive strategies in order to optimize catalyzed organic reactions for industrial applications. In this work, silica-coated magnetic nanoparticles with a core-shell type structure were prepared. The obtained material was successfully functionalized with sulfathiazole groups, which can enhance its catalytic features. The material was fully characterized, using a multi-technique approach. The catalytic performance of the as-synthesized material was evaluated in 1) the oxidation of benzyl alcohol to benzaldehyde and 2) the microwave-assisted alkylation of toluene with benzyl chloride. Remarkable conversion and selectivity were obtained for both reactions and a clear improvement of the catalytic properties was observed in comparison with unmodified γ-Fe2O3/SiO2 and γ-Fe2O3. Noticeably, the catalyst displayed outstanding magnetic characteristics which facilitated its recovery and reusability.

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“…15 Among green transformations, light-assisted oxidations using air or molecular oxygen (O2) as the oxidant represents an interesting example, as it has been shown that the SPR excited hot electrons can efficiently activate molecular oxygen. [16][17][18][19] In addition to the metal nanoparticles or active phase, it is well-established that optimizing metal-support interactions is an efficient strategy to the improvement of performances in nanocatalysis. 20,21 Among the several supports, CeO2 has been widely employed in oxidation reactions due to its oxygen mobility and storage properties, which can be further enhanced at the metal-support interface due to metal-support interactions.…”

Section: Introductionmentioning

confidence: 99%

Marrying SPR excitation and metal–support interactions: unravelling the contribution of active surface species in plasmonic catalysis

et al. 2018

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Plasmonic catalysis takes advantage of the surface plasmon resonance (SPR) excitation to drive or accelerate chemical transformations. In addition to the plasmonic component, the control over metal-support interactions in these catalysts is expected to strongly influence the performances. For example, CeO2 has been widely employed towards oxidation reactions due to its oxygen mobility and storage properties, which allow for the formation of Ce3+ sites and adsorbed oxygen species from metal-support interactions. It is anticipated that these species may be activated by the SPR excitation and contribute to the catalytic activity of the material. Thus, a clear understanding of the role played by the SPR-mediated activation of surface oxide species at the metal-support interface is needed in order to take advantage of this phenomenon. Herein, we describe and quantify the contribution from active surface oxide species at the metal-support interface (relative to O2 from air) to the activities in green SPR-mediated oxidation reactions. We employed CeO2 decorated with Au NPs (Au/CeO2) as a model plasmonic catalyst and the oxidation of p-aminothiophenol (PATP) and aniline as proof-of-concept transformations. We compared the results with SiO2 decorated with Au NPs (Au/SiO2), in which the formation of surface oxide species at the metal-support interface is not expected. We found that the SPR-mediated activation of surface oxide species at the metal-support interface in Au/CeO2 played a pivotal role in the detected activities, being even higher than the contribution coming from the activation of O2 from air.

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Photocatalytic Oxidation of Benzyl Alcohol by Homogeneous CuCl₂/Solvent: A Model System to Explore the Role of Molecular Oxygen

Cited by 84 publications

References 37 publications

Aerobic C–C Bond Cleavage of Indoles by Visible‐Light Photoredox Catalysis with Ru(bpy)₃²⁺

Aerobic C–C Bond Cleavage of Indoles by Visible‐Light Photoredox Catalysis with Ru(bpy)₃²⁺

Versatile Sulfathiazole-Functionalized Magnetic Nanoparticles as Catalyst in Oxidation and Alkylation Reactions

Marrying SPR excitation and metal–support interactions: unravelling the contribution of active surface species in plasmonic catalysis

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Photocatalytic Oxidation of Benzyl Alcohol by Homogeneous CuCl2/Solvent: A Model System to Explore the Role of Molecular Oxygen

Cited by 84 publications

References 37 publications

Aerobic C–C Bond Cleavage of Indoles by Visible‐Light Photoredox Catalysis with Ru(bpy)32+

Aerobic C–C Bond Cleavage of Indoles by Visible‐Light Photoredox Catalysis with Ru(bpy)32+

Versatile Sulfathiazole-Functionalized Magnetic Nanoparticles as Catalyst in Oxidation and Alkylation Reactions

Marrying SPR excitation and metal–support interactions: unravelling the contribution of active surface species in plasmonic catalysis

Contact Info

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Photocatalytic Oxidation of Benzyl Alcohol by Homogeneous CuCl₂/Solvent: A Model System to Explore the Role of Molecular Oxygen

Aerobic C–C Bond Cleavage of Indoles by Visible‐Light Photoredox Catalysis with Ru(bpy)₃²⁺

Aerobic C–C Bond Cleavage of Indoles by Visible‐Light Photoredox Catalysis with Ru(bpy)₃²⁺