Alternating Current Electrolysis for Organic Electrosynthesis: Trifluoromethylation of (Hetero)arenes

Rodrigo, Sachini; Um, Chanchamnan; Mixdorf, Jason C.; Gunasekera, Disni; Nguyen, Hien M.; Luo, Long

doi:10.1021/acs.orglett.0c01906

Cited by 106 publications

(98 citation statements)

References 38 publications

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“…The transition time from one type of steady state (anodic) to the other opposite steady state (cathodic) may take time and can affect product yields and reaction pathway. Rodrigo et al [40] . report a high yield for the trifluoromethylation of heteroarenes by employing AC electrosynthesis.…”

Section: Reactor and Electrode Developments For Paired Electrosynthesismentioning

confidence: 99%

Recent Advances in Paired Electrosynthesis

Marken

Cresswell

Bull

2021

The Chemical Record

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Progress in electroorganic synthesis is linked to innovation of new synthetic reactions with impact on medicinal chemistry and drug discovery and to the desire to minimise waste and to provide energy‐efficient chemical transformations for future industrial processes. Paired electrosynthetic processes that combine the use of both anode and cathode (convergent or divergent) with minimal (or without) intentionally added electrolyte or need for additional reagents are of growing interest. In this overview, recent progress in developing paired electrolytic reactions is surveyed. The discussion focuses on electrosynthesis technology with proven synthetic value for the preparation of small molecules. Reactor types are contrasted and the concept of translating light‐energy driven photoredox reactions into paired electrolytic reactions is highlighted as a newly emerging trend.

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Section: Reactor and Electrode Developments For Paired Electrosynthesismentioning

confidence: 99%

Recent Advances in Paired Electrosynthesis

Marken

Cresswell

Bull

2021

The Chemical Record

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“…When the voltage is reversed, the intermediate is oxidized to allylic cation, and subsequent deprotonation results in the final product. Instead of paired electrolysis, the ACE method gives a better yield of up to 84% [77]. This method successfully prepares trifluoromethylated pyrroles, arenes, furans, thiophenes, and imidazole with moderate to high yield.…”

Section: Electrosynthesis Of Arenes and Heteroarenesmentioning

confidence: 99%

Recent Development of Trifluoromethyl Reagents: A Review

Bhowmick

2021

J. Sci. Res.

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Organic molecules having fluorine atom are very important since it increases the lipophilicity that is essential for drug development and additionally strong carbon-fluorine (C-F) bond makes the material unique, especially for material chemistry. Instead of elemental fluorine, recently trifluoromethylated materials (CF3) have drawn considerable attention in the agrochemical and pharmaceutical industries. In the continuous development of the trifluoromethylated reagents, over the last few decades, some trifluoromethylated reagents have been well developed and the efficiency of these reagents for incorporating CF3 group on different types of substrates are also studied. In this article, all types of available trifluoromethylated reagents and their effectiveness on suitable substrates are summarized. Additionally, the methods of synthesizing trifluoromethylated substrates are discussed. Finally, the scopes of the development of new reagents after focusing on the shortcomings of the current reagents are also discussed.

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“…Finally, the screening platform should accommodate recent advancements such as electrophotochemistry 2 , 30 and alternating current electrolysis. 31 − 33 Notably, despite significant recent advances, a general, standardized HTE reactor that satisfies these desirable criteria remains elusive. 34 …”

Section: Introductionmentioning

confidence: 99%

Unlocking the Potential of High-Throughput Experimentation for Electrochemistry with a Standardized Microscale Reactor

et al. 2021

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Organic electrochemistry has emerged as an enabling and sustainable technology in modern organic synthesis. Despite the recent renaissance of electrosynthesis, the broad adoption of electrochemistry in the synthetic community, and especially in industrial settings, has been hindered by the lack of general, standardized platforms for high-throughput experimentation (HTE). Herein, we disclose the design of the HT e – Chem, a high-throughput microscale electrochemical reactor that is compatible with existing HTE infrastructure and enables the rapid evaluation of a broad array of electrochemical reaction parameters. Utilizing the HT e – Chem to accelerate reaction optimization, reaction discovery, and chemical library synthesis is illustrated using a suite of oxidative and reductive transformations under constant current, constant voltage, and electrophotochemical conditions.

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Alternating Current Electrolysis for Organic Electrosynthesis: Trifluoromethylation of (Hetero)arenes

Cited by 106 publications

References 38 publications

Recent Advances in Paired Electrosynthesis

Recent Advances in Paired Electrosynthesis

Recent Development of Trifluoromethyl Reagents: A Review

Unlocking the Potential of High-Throughput Experimentation for Electrochemistry with a Standardized Microscale Reactor

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