Visible light-driven carbon-carbon reductive coupling of aromatic ketones activated by Ni-doped CdS quantum dots: An insight into the mechanism

Hu, Rong; Xie, Weihua; Wang, Hongyan; Guo, Xinai; Sun, Huaming; Li, Chengbo; Zhang, Xuepeng; Cao, Rui

doi:10.1016/j.apcatb.2021.120946

Cited by 21 publications

(13 citation statements)

References 94 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In another control experiment, the reaction of benzaldehyde in O-deuterated isopropanol gave a product labeled with two deuterium atoms, which confirmed the two-stage of electron transfer and protonation in the reaction (Supporting Information, Scheme S3 and Figure S14). Under the O 2 environment, the desired product was formed at a very low yield due to the radical removal nature 58 of O 2 (Supporting Information, Scheme S4). This experiment clearly shows the involvement of radical intermediate in the transformation.…”

Section: Electrochemical/photo-electrochemical Studiesmentioning

confidence: 99%

Photosensitized Radical-Anion-Driven Metal-Free Selective Reduction of Aldehydes Using Graphene Oxide as an Electron Relay Mediator under Visible Light

Saini

Kumar

Sethi

et al. 2023

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

Despite the modern boost, developing a new photocatalytic system for the reduction of aldehydes is still challenging due to their high negative reduction potential. Herein, we have used a metal-free photoinduced electron-transfer system based on a cheap and readily available organic dye eosin Y (EY), graphene oxide (GO), and ammonium oxalate (AO) for photocatalytic reduction of structurally diverse aldehydes under sustainable conditions. The protocol shows remarkable selectivity for the photocatalytic reduction of aldehydes over ketones. The decisive interaction of GO and AO with the various states of EY (ground, singlet, triplet, and radical anions), which are responsible for the commencement of the reaction, was examined by various theoretical, optical, electrochemical, and photo-electrochemical studies. The synergetic system of GO, EY, and AO is appropriate for enhancing the separation efficiency of visible-light-induced charge carriers. GO nanosheets act as an electron reservoir to accept and transport photogenerated electrons from the photocatalytic system to the reactant. The reduction of the GO during the process ruled out the back transfer of photoexcited charges. Control experiments explained that the reaction involves two stages: electron transfer and protonation. This process eliminates the necessity of precious-metal-based photocatalysts or detrimental sacrificial agents and overcomes the redox potential limitations for the photoreduction of aldehydes.

show abstract

Section: Electrochemical/photo-electrochemical Studiesmentioning

confidence: 99%

Photosensitized Radical-Anion-Driven Metal-Free Selective Reduction of Aldehydes Using Graphene Oxide as an Electron Relay Mediator under Visible Light

Saini

Kumar

Sethi

et al. 2023

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

show abstract

“…Hu et al show that the reductive coupling of aromatic ketones can be catalyzed by a low-cost Ni-doped CdS QDs using TEA as the H donor with high conversion and selectivity under visible-light irradiation. [43] The authors consider that the formation of ketyl radical, which is produced via the interaction of ketones with TEA, is the key to achieve CÀ C hydrogenative coupling. DFT calculation reveals that the proton-coupled electron transfer (PCET) from TEA to AP is thermodynamically spontaneous process (ΔG < 0, Figure 6d).…”

Section: Coupling Reactions With Organic H Donorsmentioning

confidence: 99%

“…(f) The proposed mechanism of CÀ C pinacol coupling reaction using Ni-doped CdS QDs as the photocatalyst and TEA as the H donor. Reproduced with permission [43]. 2022, Elsevier.…”

mentioning

confidence: 99%

Heterogeneous Photocatalytic Hydrogenative Reactions Using Liquid Hydrogen Donors: Mechanisms, Catalysts Design, and Applications

Zhang

2023

Chemistry A European J

View full text Add to dashboard Cite

Heterogeneous photocatalysis is a promising approach for a wide range of hydrogenative reactions owing to the mild reaction conditions and the possibility of employing liquid hydrogen donors. Currently, the major interest is focused on the development of high performance photocatalyst materials and the expansion of reaction scope. An overview from a perspective of hydrogen donor and thus the related mechanistic understanding of the light‐induced hydrogenative reactions is rare. Here, we have categorized the photocatalytic hydrogenative reactions by the type of employed liquid hydrogen donors (hydrocarbons and water), discussed the basic criteria of hydrogen abstraction from these donors, and elaborated the design strategy of the photocatalyst materials.

show abstract

“…54 Then, CdS applied as visible light response photocatalyst for photoreduction of aromatic ketones, nitro compounds and CO 2 has been reported. 55–59…”

Section: Polar Cds Based Photocatalystsmentioning

confidence: 99%

Polar semiconductor photocatalysts with intrinsic electric fields for selective organic transformation

Huang

et al. 2023

New J. Chem.

View full text Add to dashboard Cite

show abstract

Visible light-driven carbon-carbon reductive coupling of aromatic ketones activated by Ni-doped CdS quantum dots: An insight into the mechanism

Cited by 21 publications

References 94 publications

Photosensitized Radical-Anion-Driven Metal-Free Selective Reduction of Aldehydes Using Graphene Oxide as an Electron Relay Mediator under Visible Light

Photosensitized Radical-Anion-Driven Metal-Free Selective Reduction of Aldehydes Using Graphene Oxide as an Electron Relay Mediator under Visible Light

Heterogeneous Photocatalytic Hydrogenative Reactions Using Liquid Hydrogen Donors: Mechanisms, Catalysts Design, and Applications

Polar semiconductor photocatalysts with intrinsic electric fields for selective organic transformation

Contact Info

Product

Resources

About