Electrochemical Deprotection of<i>para</i>-Methoxybenzyl Ethers in a Flow Electrolysis Cell

Green, Robert A.; Jolley, Katherine E.; Al-Hadedi, Azzam A. M.; Pletcher, Derek; Harrowven, David C.; Frutos, Óscar de; Mateos, Carlos; Klauber, David J.; Rincón, Juan A.; Brown, Richard C. D.

doi:10.1021/acs.orglett.7b00641

Cited by 46 publications

(46 citation statements)

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“…An application of this electrochemical process is the oxidative cleavage of para -methoxybenzyl (PMB) ethers. 278 Brown and co-workers recently detailed an electrochemical protocol for the removal PMB protecting group in flow reactors (Figure 17A). The reaction mass efficiency and atom economy scores of this deprotection process compare favorably with common chemical methods involving strong oxidants such as CAN; other common alcohol protecting groups were tolerated.…”

Section: Anodic Oxidationmentioning

confidence: 99%

“…The reaction mass efficiency and atom economy scores of this deprotection process compare favorably with common chemical methods involving strong oxidants such as CAN; other common alcohol protecting groups were tolerated. 278 Wang and co-workers demonstrated that the benzyl cation arising from direct anodic oxidations could be intercepted with water whereupon further oxidation of the resulting benzyl alcohol furnishes the ketone (Figure 17B). 279 This process is most effective for methylene units substituted with two arenes; lower yields were noted otherwise.…”

Section: Anodic Oxidationmentioning

confidence: 99%

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Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

2017

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Section: Anodic Oxidationmentioning

confidence: 99%

Section: Anodic Oxidationmentioning

confidence: 99%

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

2017

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“…It is a commercial large electrolysis flow cell designed for multigram scale syntheses composed of a spiral flow channel sandwiched in between carbon polymer and stainless-steel electrodes and separated by a polymer spacer (Author Anonymous, nd, 2020). The performance of the flow cell was exemplified by various reactions, such as the methoxylation of N-formylpyrrolidine and deprotection of PMB (para-methoxybenzyl) ethers (Green et al, 2016(Green et al, , 2017.…”

Section: Continuous Flow Chemistry and Flow Electrosynthesismentioning

confidence: 99%

Bridging Lab and Industry with Flow Electrochemistry

2020

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A revitalization of organic electrosynthesis has incited the organic chemistry community to adopt electrochemistry as a green and cost-efficient method for activating small molecules to replace highly toxic and expensive redox chemicals. However, many of the critical challenges of batch electrosynthesis, especially for organic synthesis, still remain. The combination of continuous flow technology and electrochemistry is a potent means to enable industry to implement large scale electrosynthesis. Indeed, flow electrosynthesis helps overcome problems that mainly arise from macro batch electro-organic systems, such as mass transfer, ohmic drop, and selectivity, but this is still far from being a flawless and generic applicable process. As a result, a notable increase in research on methodology and hardware sophistication has emerged, and many hitherto uncharted chemistries have been achieved. To better help the commercialization of widescale electrification of organic synthesis, we highlight in this perspective the advances made in large-scale flow electrosynthesis and its future trajectory while pointing out the main challenges and key improvements of current methodologies.

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“…[22][23][24] Electrochemical reactors with long spiral channels up to 2 m in length were subsequently developed to increase production rates to a few grams per hour. 13,19,25 However, the use of 2D planar electrodes requires that the reactor have a relatively large volume to achieve a high level of productivity.…”

Section: Introductionmentioning

confidence: 99%

Metal Nanowire Felt As a Flow-through Electrode for High-Throughput Electrosynthesis

Wiley,

Kim

2019

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Felt as a Flow-Through Electrode for High-Throughput Electrosynthesis. ChemRxiv. Preprint. The low productivity of organic electrosynthesis limits the adoption of this green methodology for production of organic chemicals. This work examines to what extent reducing the size of the fibers in a flow-through electrode to the nanoscale can increase the productivity of electrosynthesis. A Cu nanowire felt, made from nanowires 45 times smaller than the 10-μm-wide fibers in carbon paper, achieved a productivity 278 times higher than carbon paper for mass transport-limited reduction of Cu ions. For an intramolecular cyclization reaction that was limited by both mass and charge transfer kinetics, the Cu nanowire felt achieved a productivity 4.2 times higher than carbon paper. This work demonstrates large gains in productivity can be achieved with nanostructured flow-through electrodes, but that potential gains can be limited by charge transfer kinetics. File list (2) download file view on ChemRxiv Main-Cu NW electrode-12142018.pdf (855.74 KiB) download file view on ChemRxiv SI-Cu NW electrode-12142018.pdf (1.31 MiB)

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Electrochemical Deprotection ofpara-Methoxybenzyl Ethers in a Flow Electrolysis Cell

Cited by 46 publications

References 51 publications

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

Bridging Lab and Industry with Flow Electrochemistry

Metal Nanowire Felt As a Flow-through Electrode for High-Throughput Electrosynthesis

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