Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate

Senboku, Hisanori; Hayama, Mizuki; Matsuno, Hidetoshi

doi:10.3762/bjoc.18.105

Cited by 4 publications

(2 citation statements)

References 35 publications

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“…The quasi-divided cell merges the feature of the undivided and divided electrochemical cells. Usually, the quasi-divided cell ( Senboku et al, 2022 ) constitutes electrodes with two different surface areas and galvanostatic electrolysis under a low current. The two different electrodes are subjected to different environments.…”

Section: Basic Requirements For Electroorganic Synthesismentioning

confidence: 99%

Electrochemical organic reactions: A tutorial review

et al. 2023

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Although the core of electrochemistry involves simple oxidation and reduction reactions, it can be complicated in real electrochemical organic reactions. The principles used in electrochemical reactions have been derived using physical organic chemistry, which drives other organic/inorganic reactions. This review mainly comprises two themes: the first discusses the factors that help optimize an electrochemical reaction, including electrodes, supporting electrolytes, and electrochemical cell design, and the second outlines studies conducted in the field over a period of 10 years. Electrochemical reactions can be used as a versatile tool for synthetically important reactions by modifying the constant electrolysis current.

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Section: Basic Requirements For Electroorganic Synthesismentioning

confidence: 99%

Electrochemical organic reactions: A tutorial review

et al. 2023

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“…cation-pool strategy, large excess of substrate/nucleophile, or special electrochemical cell design. 23,24 Indirect electrolysis using oxidative mediators has also proven to be a powerful strategy, particularly for Shono-type C-C bond formation. 25,26 Despite these approaches, using nitrogen-based nucleophiles is scarce.…”

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confidence: 99%

A Voltage-Controlled Strategy for Modular Shono-Type Amination

Su,

Guo,

Parnitzke

et al. 2024

Preprint

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Shono-type oxidation to generate functionalized heterocycles is a powerful method for late-stage diversification of relevant pharmacophores; how-ever, development beyond oxygen-based nucleophiles remains underdeveloped. The limited scope can often be ascribed to constant current electrolysis resulting in potential drifts that oxidize a desired nucleophilic partner. Herein, we report a voltage-controlled strategy to selectively oxidize a broad scope of substrates, enabling modular C–N bond formation from protected amine nucleophiles. We implement an electroanalytically-guided workflow using cyclic voltammetry (CV) and differential pulse voltammetry (DPV) to identify oxidation potentials across a range of heterocyclic substrates. Controlled potential electrolysis (CPE) selectively generates -functionalized C–N products in moderate to good yields using carbamate-, sulfonamide-, and benzamide-derived nucleophiles. The importance of voltage control is further exemplified in two cases: (1) change in selectivity at different potentials with a morpholine substrate and (2) analysis of reaction outcomes between Celecoxib and an N-Boc or N-Ns-pyrrolidine substrate; the latter requires a potential more anodic than Celecoxib and does not yield desired product. Lastly, sequential voltage-controlled C–N and C–O functionalization of a model substrate generates difunctionalized pyrrolidines further broadening the utility of this reaction.

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Electrifying Friedel–Crafts Intramolecular Alkylation toward 1,1-Disubstituted Tetrahydronaphthalenes

Lunghi,

Ronco,

Della Negra

et al. 2023

J. Org. Chem.

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In this work, we successfully employed electrochemical conditions to promote a Hofer–Moest, intramolecular Friedel–Crafts alkylation sequence. The reaction proceeds under mild conditions, employing carboxylic acids as starting materials. Notably, the electrochemical process performed in batch was adapted to a continuous flow electrolysis apparatus to provide a significant improvement. This catalyst-free, electrochemical approach produces an array of tetrahydronaphthalenes that could be used for API synthesis.

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Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate

Cited by 4 publications

References 35 publications

Electrochemical organic reactions: A tutorial review

Electrochemical organic reactions: A tutorial review

A Voltage-Controlled Strategy for Modular Shono-Type Amination

Electrifying Friedel–Crafts Intramolecular Alkylation toward 1,1-Disubstituted Tetrahydronaphthalenes

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