Efficient photoelectrochemical Kolbe C–C coupling at BiVO<sub>4</sub> electrodes under visible light irradiation

Swansborough-Aston, William A.; Soltan, Ayman; Coulson, Ben; Pratt, Andrew; Chechik, Victor; Douthwaite, Richard E.

doi:10.1039/d2gc04423d

Cited by 5 publications

(3 citation statements)

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“…Douthwaite and Chechik recently documented a work involving an interfacial photoelectrochemical Kolbe CÀ C coupling utilizing BiVO 4 electrodes, achieved through the oxidative decarboxylation of carboxylic acids (Figure 2, III). [15] Significantly, their research uncovered that maintaining high substrate concentrations plays a crucial role in stabilizing the double layer, eliminating the need for additional supporting electrolytes. These findings can be contrasted with closely related photocatalytic Kolbe processes employing powdered semiconductor photocatalysts.…”

Section: Interfacial Photoelectrochemistry (Ipec) Catalysis In Organi...mentioning

confidence: 99%

“…Moreover, a diverse range of heteroarenes were successfully functionalized using primary, secondary, and tertiary alkyltrifluoroborates, showcasing excellent regio-and chemoselectivity of the desired product (14) (Figure 4, I). In 2021, the same group introduced an advanced photoelectrocatalytic technique designed for the dehydrogenative cross-coupling of electron-rich arenes with azoles, producing the CÀ N formation product (15). [24] This feat was achieved by incorporating MesÀ Acr + as the photocatalyst, marking yet another significant advancement.…”

Section: Organic Electrochemically Recycled Photocatalystsmentioning

confidence: 99%

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Synergistic Photoredox and Electrochemical Catalysis in Organic Synthesis and Late‐Stage Functionalizations

Sun,

Lin,

Chen

et al. 2024

ChemCatChem

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This review delves into the innovative field of interfacial photoelectrochemical (iPEC) and photoelectrochemical (PEC) catalysis, the dynamic synthesis methodologies that seamlessly integrates electrochemical and photoredox catalysis for efficient and environmentally friendly reactions. Utilizing minute quantities of photocatalysts, visible light becomes a powerful tool, generating transient excited states to catalyze a spectrum of reactions through single‐electron oxidation or reduction events. The review categorizes recent advancements, highlighting applications in organic synthesis, late‐stage modifications, and the distinctive features of photoelectrochemical methodology. Despite being in its early stages, this synergistic approach holds great promise for propelling organic synthesis forward, with potential applications in large‐scale synthesis and diverse late‐stage functionalizations, including asymmetric catalysis and bioconjugation strategies for biomolecule modifications.

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Section: Interfacial Photoelectrochemistry (Ipec) Catalysis In Organi...mentioning

confidence: 99%

Section: Organic Electrochemically Recycled Photocatalystsmentioning

confidence: 99%

Synergistic Photoredox and Electrochemical Catalysis in Organic Synthesis and Late‐Stage Functionalizations

Sun,

Lin,

Chen

et al. 2024

ChemCatChem

View full text Add to dashboard Cite

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“…Substrate concentration was also an arresting factor that affected the reaction rate [77]. Consequently, it was important to explore the influence of feedstock concentration.…”

Section: Influence Of Substance Concentration On Catalytic Activitymentioning

confidence: 99%

Integrating Fermentation Engineering and Organopalladium Chemocatalysis for the Production of Squalene from Biomass-Derived Carbohydrates as the Starting Material

Wu,

Tian,

Guo

et al. 2023

Catalysts

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The transition from fossil resources to renewable biomass for the production of valuable chemicals and biobased fuels is a crucial step towards carbon neutrality. Squalene, a valuable chemical extensively used in the energy, healthcare, and pharmaceutical fields, has traditionally been isolated from the liver oils of deep-sea sharks and plant seed oils. In this study, a biochemical synergistic conversion strategy was designed and realized to convert glucose to squalene by combining fermentation technology in yeast with reductive coupling treatment of dienes. First, glucose derived from hydrolysis of cellulose was used as a renewable resource, using genetically engineered Saccharomyces cerevisiae as the initial biocatalyst to produce β-farnesene with a titer of 27.6 g/L in a 2.5 L bioreactor. Subsequently, intermediate β-farnesene was successfully converted to squalene through the organopalladium-catalyzed reductive coupling reaction involving the formation of Pd(0)L2 species. Under mild reaction conditions, impressive β-farnesene conversion (99%) and squalene selectivity (100%) were achieved over the Pd(acac)2 catalyst at a temperature of 75 °C in an ethanol solvent after 5 h. This advancement may provide insights into broadening squalene production channels and accessing the complex skeletons of natural terpenoids from biorenewable carbon sources, offering practical significance and economic benefits.

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Customized Photoelectrochemical C−N and C−P Bond Formation Enabled by Tailored Deposition on Photoanodes

Wang,

Yang,

Gao

et al. 2024

Angewandte Chemie

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Photoelectrochemistry (PEC) is burgeoning as an innovative solution to organic synthesis. However, the current PEC system suffers limited reaction types and unsatisfactory performances. Herein, we employ efficient BiVO4 photoanode with tailored deposition layers for customizing two PEC approaches toward C–N and C–P formation. Notably, our process proceeds under mild reaction conditions, easily available substrates, and ultra‐low potentials. Beyond photocatalysis and electrocatalysis, customized PEC offers high efficiency, good functional group tolerance, and substantial applicability for decorating drug molecules, highlighting its promising potential to enrich the synthetic toolbox for broader organic chemistry of practical applications.

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Efficient photoelectrochemical Kolbe C–C coupling at BiVO₄ electrodes under visible light irradiation

Abstract: Electrochemical Kolbe C-C coupling of carboxylic acids at Pt electrodes has been studied for over 150 years and remains relevant today because renewable electricity is envisaged to make an increasing...

Cited by 5 publications

References 73 publications

Synergistic Photoredox and Electrochemical Catalysis in Organic Synthesis and Late‐Stage Functionalizations

Synergistic Photoredox and Electrochemical Catalysis in Organic Synthesis and Late‐Stage Functionalizations

Integrating Fermentation Engineering and Organopalladium Chemocatalysis for the Production of Squalene from Biomass-Derived Carbohydrates as the Starting Material

Customized Photoelectrochemical C−N and C−P Bond Formation Enabled by Tailored Deposition on Photoanodes

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Efficient photoelectrochemical Kolbe C–C coupling at BiVO4 electrodes under visible light irradiation

Abstract: Electrochemical Kolbe C-C coupling of carboxylic acids at Pt electrodes has been studied for over 150 years and remains relevant today because renewable electricity is envisaged to make an increasing...

Cited by 5 publications

References 73 publications

Synergistic Photoredox and Electrochemical Catalysis in Organic Synthesis and Late‐Stage Functionalizations

Synergistic Photoredox and Electrochemical Catalysis in Organic Synthesis and Late‐Stage Functionalizations

Integrating Fermentation Engineering and Organopalladium Chemocatalysis for the Production of Squalene from Biomass-Derived Carbohydrates as the Starting Material

Customized Photoelectrochemical C−N and C−P Bond Formation Enabled by Tailored Deposition on Photoanodes

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Efficient photoelectrochemical Kolbe C–C coupling at BiVO₄ electrodes under visible light irradiation