First Pinacol Coupling in Emulsified Water: Key Role of Surfactant and Impact of Alternative Activation Technologies

Billamboz, Muriel; Len, Christophe

doi:10.1002/cssc.201500108

Cited by 11 publications

(4 citation statements)

References 84 publications

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“…To evaluate the efficiency of novel oxidative counter reactions, a model cathodic reaction is necessary. The pinacol coupling is one of the most important reactions for the reductive formation of carbon–carbon bonds, and thus, the corresponding synthetic methods have been substantially explored. − Notably, Manchanayakage and co-workers reported an electrochemical pinacol coupling, fitted with a sacrificial tin foil anode, but the use of sacrificial metal anode would suffer from narrow substrate scope, environmental concerns, and infeasible scale-up. Recently, Zhang and co-workers disclosed an electrochemical pinacol coupling coupled with OER in a divided cell, although the high overpotentials of the OER process led to the additional requirements, such as potentiostatic setup, alkaline condition, and so forth.…”

Section: Introductionmentioning

confidence: 99%

Discovery of Anodic Thiourea Oxidation as a Sustainable Counter Reaction to Boost Electro-Reductive Organic Transformations

Wang

Shonhe

et al. 2023

ACS Sustainable Chem. Eng.

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In the reductive electrochemistry, the oxidative counter reaction remains one of the main bottlenecks for efficient cathodic organic transformations, but it has received less attention. Herein, anodic thiourea (TU) oxidation is reported as a sustainable oxidative counter reaction, which takes place at a low potential with a relative high current density. Mechanistic studies suggest that the anodic TU oxidation is initiated by a single electron-transfer (SET) process with the formation of formamidine disulfide cation as the main intermediate. In practice, the anodic TU oxidation counterbalances a series of SET reductive transformations at the cathode, and the protocol features sustainable condition, minimized waste, convenient setup, and excellent scalability, which highlights the underexplored potential of TU oxidation as an alternative counter reaction for the reductive electrochemistry.

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Section: Introductionmentioning

confidence: 99%

Discovery of Anodic Thiourea Oxidation as a Sustainable Counter Reaction to Boost Electro-Reductive Organic Transformations

Wang

Shonhe

et al. 2023

ACS Sustainable Chem. Eng.

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“…Surfactants are amphiphilic substances that enable hydrophobic substances to come into closer contact with highly polar substances, producing products. [9][10][11][12] Various surfactant properties, such as concentration, temperature, and polarity of relative surfactants, are important for the successful completion of reactions. [13][14][15][16] Most organic reactions occur at the surfactant's CMC.…”

Section: Introductionmentioning

confidence: 99%

Surfactant‐Mediated Synthesis of Methylene Bridged 6‐Aminouracils: Development of a Greener Protocol, Water Remediation and Preliminary Biological Screening

Mal,

Das

2023

ChemistrySelect

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Herein, we describe a surfactant‐catalyzed green methodology for electrophilic substitution reaction of 6‐aminouracil derivatives with various aldehydes that were neither reported earlier nor produced using conventional routes. Optimized results show the importance of anionic surfactant (SDS) on the reaction between hydrophilic and hydrophobic compounds in aqueous medium. All synthesized compounds were characterized by various spectroscopic methods like FTIR, NMR, HRMS, and SC‐XRD. Furthermore, the surfactant remediation from the reaction mixture was done using graphene oxide (GO). The results from batch‐adsorption studies indicate prominent sorption of SDS onto the surface of GO with an adsorption efficiency of ~84.9 %. The SDS adsorbed onto GO were analyzed using UV‐vis, FT‐IR, Raman, and HRTEM analysis. Next, the synthesized compounds were screened for their potential anti‐SARS‐CoV2 activity due to their structural resemblance with pyrimidine analogs acting as anti‐viral agents. The in‐silico results indicate that the synthesized compounds exhibit the highest inhibitory activity towards RdRp with binding energy −9.55 kcal/mol. In contrast, Remdesivir showed only −6.45 kcal/mol. In addition, upon preliminary screening of the compounds for possible antimicrobial activity (antifungal and anti‐leishmanial), 4 bf showed moderately high inhibitory activity with IC50 values of 205.48 μM and 124.97 μM for fungal and leishmanial strains, respectively.

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“…Ti, V, or Zr complexes have also been widely used to promote this reaction . In the framework of green chemistry, our research group focused on this particular reaction and several batch sustainable methodologies have been reported: (i) micellar catalysis under sonication, (ii) use of commercially available acidic resins or use of only acidic water . Due to our interest and the first encouraging results, a continuous flow system for selective pinacol coupling reactions was envisaged.…”

Section: Introductionmentioning

confidence: 99%

Selective Pinacol-Coupling Reaction using a Continuous Flow System

et al. 2016

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The first continuous flow pinacol coupling reaction of carbonyl compounds was successfully achieved within only 2 min during a single pass through a cartridge filled with zinc(0). The optimized method allowed the efficient production of gram-scale value-added compounds with high productivity. The developed methodology is efficient for aromatic or α,β-unsaturated aldehydes but gives moderate results for more stable acetophenone derivatives. Moreover, the flow method displayed better results in terms of yield and selectivity in comparison to the corresponding batch methodology.

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First Pinacol Coupling in Emulsified Water: Key Role of Surfactant and Impact of Alternative Activation Technologies

Cited by 11 publications

References 84 publications

Discovery of Anodic Thiourea Oxidation as a Sustainable Counter Reaction to Boost Electro-Reductive Organic Transformations

Discovery of Anodic Thiourea Oxidation as a Sustainable Counter Reaction to Boost Electro-Reductive Organic Transformations

Surfactant‐Mediated Synthesis of Methylene Bridged 6‐Aminouracils: Development of a Greener Protocol, Water Remediation and Preliminary Biological Screening

Selective Pinacol-Coupling Reaction using a Continuous Flow System

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