Chemo‐ and Diastereoselectivities in the Electrochemical Reduction of Maleimides

Rix, Kathryn; Kelsall, G. H.; Hellgardt, Klaus; Hii, King Kuok

doi:10.1002/cssc.201403184

Cited by 4 publications

(3 citation statements)

References 34 publications

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“…23 As a wider program of research in the development of effective flow strategies for redox transformations, we have previously described the use of an electrochemical flow cell for the chemoselective reduction of the CC bond in maleimide derivatives. 24 The use of a prototype lab-scale reactor is described in this paper, for the production of ammonium persulfate by the electrolysis of aqueous solution of ammonium sulfate with a BDD anode (Figure 1), operated under batch recirculation mode. Gas counters were incorporated with each of the reservoirs to monitor the liberation of gaseous byproducts (H 2 and O 2 at the cathode and anode, respectively).…”

Section: ■ Introductionmentioning

confidence: 99%

Toward a Green Generation of Oxidant on Demand: Practical Electrosynthesis of Ammonium Persulfate

Zhu

Hii

Hellgardt

2016

ACS Sustainable Chem. Eng.

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The electrolysis of aqueous solution of ammonium sulfate has been systematically investigated in a two-compartment electrolytic flow cell for the potential applications for green and efficient synthesis of ammonium persulfate. A commercial boron-doped diamond (BDD) coated anode (active area of 10 cm 2 ) was used and electrolysis was operated under batch recirculation. Under a flow rate of 3.33 mL min −1 , the flow pattern is well described by a flow model with axial dispersion in the reaction compartment. The electrosynthesis was found not to be mass transport-limited in the present system at flow rates of ≥50 mL min −1 with a current density of ≤150 mA cm −2 . The charge transfer-controlled reaction was subsequently modeled, taking into account bubble coverage effects. Thereafter, the productivity of persulfate was investigated under different current densities, electrolyte compositions and concentrations. It was found that a high current efficiency can be obtained at the initial stage (∼93%, 150 mA cm −2 , ≤1 h), which deteriorated with time. By altering the volume and concentration of the anolyte, up to 1.31 M (150 mA cm −2 , 3 h) of oxidant solution can be delivered for ondemand applications. The hydrogen of high purity was produced as a valuable byproduct of the process.

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Section: ■ Introductionmentioning

confidence: 99%

Toward a Green Generation of Oxidant on Demand: Practical Electrosynthesis of Ammonium Persulfate

Zhu

Hii

Hellgardt

2016

ACS Sustainable Chem. Eng.

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“…The authors have cited additional references within the Supporting Information [77–99] . Raw NMR data is available free of charge from zenodo.org: https://doi.org/10.5281/zenodo.8099632.…”

Section: Methodsmentioning

confidence: 99%

Photochemical [2+2] Cycloaddition of Alkynyl Boronates

Liashuk

Grygorenko

Volovenko

et al. 2023

Chemistry A European J

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A photochemical [2+2] cycloaddition of alkynyl boronates and maleimides is reported. The developed protocol provided 35–70% yield of maleimide‐derived cyclobutenyl boronates and demonstrated wide compatibility with various functional groups. The synthetic utility of the prepared building blocks was demonstrated for a range of transformations, including Suzuki cross‐coupling, catalytic or metal‐hydride reduction, oxidation, and cycloaddition reactions. With aryl‐substituted alkynyl boronates, the products of double [2+2] cycloaddition were obtained predominantly. Using the developed protocol, a cyclobutene‐derived analogue of Thalidomide was prepared in one step. Mechanistic studies supported the participation of the triplet‐excited state maleimides and ground state alkynyl boronates in the key step of the process.

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“…The authors have cited additional references within the Supporting Information. [34][35][36][37][38][39][40][41][42][43][44][45][46][47]…”

Section: Supporting Informationmentioning

confidence: 99%

Direct Diels‐Alder Reaction of Biomass‐Derived Furfurol with Maleimides in a Bio‐Based Green Solvent

Skolia,

Kokotos

2024

Eur J Org Chem

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Environmental concern has motivated an inclination to exploit waste and upgrade it into high‐added‐value chemicals. Biomass is an excellent carbon source that provides a variety of raw materials as building blocks, such as furans. Herein, we report the upcycling of furfurol, a known biomass by‐product, through a Diels‐Alder cycloaddition with maleimides that is performed in a green bio‐derived solvent, 2‐MeTHF. We provide two alternative sets of reaction conditions to promote exo or endo selectivity, which depends on the temperature employed. A variety of products were obtained in 70‐96% yield and high exo selectivity at 80 °C, while a 30:70‐45:55 exo/endo ratio was produced at room temperature. A large‐scale reaction was also performed.

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Chemo‐ and Diastereoselectivities in the Electrochemical Reduction of Maleimides

Cited by 4 publications

References 34 publications

Toward a Green Generation of Oxidant on Demand: Practical Electrosynthesis of Ammonium Persulfate

Toward a Green Generation of Oxidant on Demand: Practical Electrosynthesis of Ammonium Persulfate

Photochemical [2+2] Cycloaddition of Alkynyl Boronates

Direct Diels‐Alder Reaction of Biomass‐Derived Furfurol with Maleimides in a Bio‐Based Green Solvent

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