Continuous-flow step-economical synthesis of thiuram disulfides <i>via</i> visible-light photocatalytic aerobic oxidation

Xu, Haoxing; Zhao, Ze-Run; Patehebieke, Yeersen; Chen, Qian-Qian; Fu, Shun-Guo; Chang, Shuai-Jun; Zhang, Xu-Xu; Zhang, Zhiliang; Wang, Xiao

doi:10.1039/d0gc04270f

Cited by 13 publications

(9 citation statements)

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“…In 2021, Wang et al reported a continuous-flow synthesis of thiuram disulfides, which are functionalities with important industrial applications . Their strategy was based on the eosin Y-mediated photooxidation of the adduct formed between CS 2 and an amine (Scheme ).…”

Section: Flow Photochemistrymentioning

confidence: 99%

“…In 2021, Wang et al reported a continuous-flow synthesis of thiuram disulfides, which are functionalities with important industrial applications. 522 Their strategy was based on the eosin Y-mediated photooxidation of the adduct formed between CS 2 and an amine (Scheme 76). Although the authors proposed a mechanism involving the superoxide radical (O 2 ) −• , experiments with diphenylisobenzofuran, which is a singlet oxygen trapping agent, proved that singlet oxygen is involved in the mechanism, as claimed by the authors.…”

Section: Singlet Oxygen-mediated Oxidationsmentioning

confidence: 99%

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Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

et al. 2021

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Photoinduced chemical transformations have received in recent years a tremendous amount of attention, providing a plethora of opportunities to synthetic organic chemists. However, performing a photochemical transformation can be quite a challenge because of various issues related to the delivery of photons. These challenges have barred the widespread adoption of photochemical steps in the chemical industry. However, in the past decade, several technological innovations have led to more reproducible, selective, and scalable photoinduced reactions. Herein, we provide a comprehensive overview of these exciting technological advances, including flow chemistry, high-throughput experimentation, reactor design and scale-up, and the combination of photo- and electro-chemistry.

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Section: Flow Photochemistrymentioning

confidence: 99%

Section: Singlet Oxygen-mediated Oxidationsmentioning

confidence: 99%

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

et al. 2021

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“…Notably, the theoretical capacity of organosulfide could be further improved by devising the end caps and increasing the number of linear S atoms. [ 20 ] The electrode‐level energy density was 376.2 Wh kg −1 , which was the highest among sulfide‐based ASSBs but the second highest when compared with SPE‐based ASSBs. This is due to the lightweight properties of SPEs compared with sulfide electrolytes.…”

Section: Resultsmentioning

confidence: 99%

Practically Accessible All‐Solid‐State Batteries Enabled by Organosulfide Cathodes and Sulfide Electrolytes

Zhang

Zheng

et al. 2022

Adv Funct Materials

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The combination of organic electrode materials and sulfide electrolytes is expected to enable the development of all-solid-state organic batteries featuring high energy density, safety, and sustainability. Here, thiuram hexasulfide is first reported as a low-cost and high-capacity cathode material for solid-state organic batteries based on sulfide electrolytes. Notably, a capacity of ≈600 mA h g −1 is delivered and the capacity retention is 80.8% after 500 cycles. An electrochemically reversible change of the cathode interface is revealed upon cycling. The full cell displays an oscillating stress change of up to 0.6 MPa during cycling, predominated by the anode side. The energy density is 1140 Wh kg −1 at the material level and 376 Wh kg −1 at the electrode level, which are among the best-reported organic cathodes to date. A high areal capacity of 10.4 mA h cm −2 is reached with a high mass loading cathode. A dry-film approach is further explored to manufacture sheet-type cells. The free-standing Li 6 PS 5 Cl film with a thickness of only 48 µm demonstrates an ultralow areal resistance of 3.9 Ω cm 2 , which significantly boosts the cell-level energy density and reduces the cell internal resistance.

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“…In the process of dehydrogenative coupling of benzyl mercaptan to form disulfides, the superoxide radical is a very critical free radical species. 52 With the stepwise addition of p -benzoquinone as a radical scavenger, the corresponding photocatalytic activity gradually weakened, indicating that the photoreaction process involves a radical pathway (Fig. S20†).…”

Section: Resultsmentioning

confidence: 99%

Polarization engineering of porous organic polymers for superior photocatalytic synthesis of disulfides and CO₂reduction

Huang

Mao

et al. 2022

J. Mater. Chem. A

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Continuous-flow step-economical synthesis of thiuram disulfides via visible-light photocatalytic aerobic oxidation

Abstract: A continuous-flow photocatalytic synthesis of the industrially important thiuram disulfides has been developed, utilizing O2 as the oxidant and Eosin Y as the photoredox catalyst.

Cited by 13 publications

References 38 publications

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

Practically Accessible All‐Solid‐State Batteries Enabled by Organosulfide Cathodes and Sulfide Electrolytes

Polarization engineering of porous organic polymers for superior photocatalytic synthesis of disulfides and CO₂reduction

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Continuous-flow step-economical synthesis of thiuram disulfides via visible-light photocatalytic aerobic oxidation

Abstract: A continuous-flow photocatalytic synthesis of the industrially important thiuram disulfides has been developed, utilizing O2 as the oxidant and Eosin Y as the photoredox catalyst.

Cited by 13 publications

References 38 publications

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

Practically Accessible All‐Solid‐State Batteries Enabled by Organosulfide Cathodes and Sulfide Electrolytes

Polarization engineering of porous organic polymers for superior photocatalytic synthesis of disulfides and CO2reduction

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Polarization engineering of porous organic polymers for superior photocatalytic synthesis of disulfides and CO₂reduction