scholarly journals Pseudo High-Throughput Development and Optimization of the Electrochemical Oxidation of Sensitive Propargylic Benzylic Alco-hols

2021 ◽  
Author(s):  
Chad Hatch ◽  
Maxwell Martin ◽  
Danielle Beam ◽  
Glenn Yap ◽  
Matthew Von Bargen ◽  
...  
Keyword(s):  
Electrochemical Oxidation ◽  
High Throughput ◽  
Electrochemical Method ◽  
Power Supplies ◽  
Complex Molecules ◽  
Benzylic Alcohols ◽  
Benzylic Alcohol ◽  
Low Efficiency ◽  
Convenient Preparation ◽  
Acute Challenge

The electrochemical oxidation of sensitive propargylic benzylic alcohols having varying substituents is reported. The ther-mal oxidation of propargylic benzylic alcohols presents an acute challenge in the synthesis of complex molecules and various traditional oxidation methods proceed with low efficiency or not at all. We describe the convenient preparation and charac-terization of N-hydroxytetrafluorophthalimide (TFNHPI) and a practical, green electrochemical oxidation protocol that em-ploys TFNHPI as a stable, efficient electrochemical mediator. The electrochemical method employing TFNHPI to oxidize propargylic benzylic alcohols was developed and optimized in pseudo high-throughput fashion using a bank of inexpensive two-electrode power supplies. The electrochemical oxidation of propargylic benzylic alcohol was also leveraged to develop efficient synthetic pathways to prepare gram quantities of resveratrol natural products such as the pauciflorols.

The Application and Research of Electrochemical Method Treating Acid Red 3R Simulation Wastewater by Response Surface Method

2013 ◽  
Vol 295-298 ◽  
pp. 1258-1262
Author(s):  
Jun Sheng Hu ◽  
Lei Guan ◽  
Jia Li Dong ◽  
Ying Wang ◽  
Ying Yong Duan
Keyword(s):  
Response Surface ◽  
Electrochemical Oxidation ◽  
Current Density ◽  
Electrochemical Method ◽  
Electrolyte Concentration ◽  
Ph Value ◽  
Removal Rate ◽  
Oxidation Method ◽  
Surface Method ◽  
Optimal Value

Using electrochemical oxidation method treats the acid red 3R simulation wastewater, investigates the influence of current density, electrolyte concentration, pH-value and aeration and their interaction on the removal rate of chroma. Through the design of Box-Benhnken Design(BBD) and the response surface analysis, the influence sequence of all variables is current density > aeration > electrolyte concentration > pH-value, the influence sequence of all interaction is electrolyte concentration-aeration > current density-aeration ,electrolyte concentration-pH value > current density-pH value > pH value-aeration > current density-electrolyte concentration. Ultimately, the optimal value is 98.4915% under the condition of current density of 6.51mA/cm2,electrolyte concentration of 0.04mol/L,pH-value of 4.17 and aeration of 0.24m3/h.

PINO/NHPI-mediated selective oxidation of cycloalkenes to cycloalkenones via a photo-electrochemical method

2019 ◽  
Vol 55 (63) ◽  
pp. 9339-9342 ◽  
Author(s):  
Hiroyuki Tateno ◽  
Yugo Miseki ◽  
Kazuhiro Sayama
Keyword(s):  
Electrochemical Oxidation ◽  
Selective Oxidation ◽  
Electrochemical Method ◽  
Applied Bias ◽  
Indirect Oxidation

The photo-electrochemical oxidation of cyclohexene to 2-cyclohexene-1-one was successfully performed with excellent Faraday efficiency (>99%) via indirect oxidation with a PINO/NHPI mediator and O2 on a BiVO4/WO3 photoanode under low applied bias.

Nanomole-scale high-throughput chemistry for the synthesis of complex molecules

Science ◽  
2014 ◽  
Vol 347 (6217) ◽  
pp. 49-53 ◽  
Author(s):  
Alexander Buitrago Santanilla ◽  
Erik L. Regalado ◽  
Tony Pereira ◽  
Michael Shevlin ◽  
Kevin Bateman ◽  
...  
Keyword(s):  
High Throughput ◽  
Scale Up ◽  
Natural Product Synthesis ◽  
Test Case ◽  
Coupling Reactions ◽  
High Throughput Analysis ◽  
Complex Molecules ◽  
Cross Coupling Reactions ◽  
High Throughput Experimentation ◽  
Palladium Catalyzed

At the forefront of new synthetic endeavors, such as drug discovery or natural product synthesis, large quantities of material are rarely available and timelines are tight. A miniaturized automation platform enabling high-throughput experimentation for synthetic route scouting to identify conditions for preparative reaction scale-up would be a transformative advance. Because automated, miniaturized chemistry is difficult to carry out in the presence of solids or volatile organic solvents, most of the synthetic “toolkit” cannot be readily miniaturized. Using palladium-catalyzed cross-coupling reactions as a test case, we developed automation-friendly reactions to run in dimethyl sulfoxide at room temperature. This advance enabled us to couple the robotics used in biotechnology with emerging mass spectrometry–based high-throughput analysis techniques. More than 1500 chemistry experiments were carried out in less than a day, using as little as 0.02 milligrams of material per reaction.

A convenient preparation of conjugated nitro olefins by electrochemical method

1983 ◽  
Vol 24 (41) ◽  
pp. 4443-4444 ◽  
Author(s):  
Atsutaka Kunai ◽  
Yasuo Yanagai ◽  
Kazuo Sasaki
Keyword(s):  
Electrochemical Method ◽  
Convenient Preparation

Determination of Platinum and Palladium in the Presence of other Metals in the Mineral Raw Materials

2016 ◽  
Vol 712 ◽  
pp. 332-337 ◽  
Author(s):  
Elvira M. Ustinova ◽  
Eduard Gorchakov
Keyword(s):  
Electrochemical Oxidation ◽  
Electrochemical Method ◽  
Raw Materials ◽  
Mineral Raw Materials ◽  
Oxidation Processes

An electrochemical method for determination of the platinum and palladium was suggested and developed in this study. The effect of accompanying elements on the electrochemical oxidation processes of platinum and palladium has been described. It has been shown that the determination of platinum and palladium is possible only after removal of sample components.

scholarly journals Scandium and Dimethylaminopyridine Catalyzed Dehydrative Coupling of Secondary Benzylic and Primary Alcohols to Synthesize Unsymmetrical Ethers

2020 ◽  
Author(s):  
Julia Duncan ◽  
Lun Li ◽  
Vahid Mohammadrezaei ◽  
Laina Geary
Keyword(s):  
Spectroscopic Data ◽  
Supplementary Information ◽  
Primary Alcohols ◽  
Benzylic Alcohols ◽  
Benzylic Alcohol ◽  
Catalytic Condensation ◽  
Rapid Formation ◽  
One Step ◽  
Insight Into ◽  
Mechanism Of The Reaction

We developed a direct catalytic condensation of benzylic alcohols and primary alcohols to synthesize unsymmetrical ethers in one step, catalyzed by scandium triflate and p-dimethylaminopyridine (DMAP). Preliminary experiments give some insight into the mechanism of the reaction, though suggest that the process is quite complex. We suspect the rapid formation of a dimer from a secondary benzylic alcohol via a carbocation intermediate precedes unsymmetrical ether formation. Full experimental details and spectroscopic data are provided as supplementary information.

scholarly journals Indirect Electrochemical Processes. 14. Indirect Electrochemical Oxidation of Benzylic Alcohols with Organic Mediators.

1983 ◽  
Vol 37b ◽  
pp. 499-507 ◽  
Author(s):  
Karl-Heinz Grosse Brinkhaus ◽  
Eberhard Steckhan ◽  
Werner Schmidt ◽  
Kjell Undheim ◽  
Curt R. Enzell ◽  
...  
Keyword(s):  
Electrochemical Oxidation ◽  
Benzylic Alcohols ◽  
Electrochemical Processes

Preparation of Biscarbonylmethylenetriphenylphosphorane Derivatives: A Mini-Review

2019 ◽  
Vol 16 (10) ◽  
pp. 769-778
Author(s):  
Andrés-Felipe Villamizar-Mogotocoro ◽  
Juan-Manuel Urbina-González ◽  
Ingrid Rincón-Valdivieso
Keyword(s):  
Biological Activity ◽  
Electrochemical Oxidation ◽  
Oxidation Products ◽  
Thermal Treatments ◽  
Reaction Conditions ◽  
Complex Molecules ◽  
High Importance

Biscarbonylmethylenetriphenylphosphoranes are versatile compounds derived from stabilized α-carbonylmethylenetriphenylphosphoranes, mainly prepared by transylidation or by analogue methodologies; other procedures include electrochemical oxidation, palladium-catalized insertions and displacements reactions with tellurol esters, as well as the use of Bestmann’s ylide with different reagents and reaction conditions. These biscarbonylmethylenetriphenylphosphoranes are usually converted into acetylenes by thermal treatments. Biscarbonylmethylenetriphenylphosphoranes and their oxidation products -vicinal tricarbonyl compounds- are of high importance due to their use as synthons of more complex molecules and their promising biological activity.

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