Electrochemical iodofluorination of electron-deficient olefins

Nagura, Hirokatsu; Kuribayashi, Shunsuke; Ishiguro, Yutaka; Inagi, Shinsuke

doi:10.1016/j.tet.2009.11.005

Cited by 16 publications

(13 citation statements)

References 12 publications

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“…DME also shows unique fluorination product selectivity (Scheme 19), 63 Recently, it was shown that nitromethane significantly promoted electrochemical iodofluorination of electron-deficient olefins such as a,b-unsaturated esters, amides, and phosphonates. 64…”

Section: Selective Electrochemical Fluorination In Organic Solventsmentioning

confidence: 99%

Selective electrochemical fluorination of organic molecules and macromolecules in ionic liquids

2011

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This article provides an outline of recent studies on selective electrochemical fluorination in ionic liquid fluoride salts toward green sustainable chemistry. First, a brief historical background of electrochemical fluorination in organic solvents is provided, and some particular problems and unique solvent effects associated with this technique are briefly mentioned. Second, recent progress in selective fluorination and fluorodesulfurization of organic molecules and macromolecules in ionic liquids using direct and indirect electrolysis with recyclable mediators is reviewed.

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Section: Selective Electrochemical Fluorination In Organic Solventsmentioning

confidence: 99%

Selective electrochemical fluorination of organic molecules and macromolecules in ionic liquids

2011

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“…These organic basic HF sources are readily soluble in organic solvent, and these solutions are sufficiently conductive that supporting electrolyte is often not required due to their (partial) ionic nature. Thus, the combination of anodic oxidation and hydrogen fluoride has been used for the fluorination of alkenes, [7,[17][18][19][20][21][22][23][24][25] alkynes, [18] aromatic rings, [26][27][28][29] esters, [30][31][32] ketones [16,33] and thioketals, [34][35][36][37][38] among others, Figure 1A. Warning: Extreme care should always still be used in handling these materials; handle only in a fume hood, wear safety goggles or a face shield, and wear appropriate impermeable clothing.…”

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confidence: 99%

3D Printed Reactionware for Synthetic Electrochemistry with Hydrogen Fluoride Reagents

2021

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Electrochemical fluorination reactions of organic compounds frequently employ hydrogen fluoride reagents that are corrosive. The corrosive nature of these reagents necessitates either the construction or purchase of cells that are stable to hydrogen fluoride, which require high-cost materials, machining time and expertise. Herein, we offer an alternative solution using 3D printing, which is an inexpensive and rapid manufacturing technique. We have designed, printed and shared four different cell types in polypropylene and tested them in an electrochemical alkene difluorination reaction in the presence of triethylamine • 3HF and pyridinium poly • (HF).

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“…334,335 Moreover, regioselective electrochemical monofluorination has also been reported for a collection of oxygen-containing heterocycles, including carbonates, 336,337 chroman-4-ones, [338][339][340] esters, 337 ethers 336,337 and lactones. 336,337 Additionally, electrochemical protocols for accomplishing fluorodesulfurization, [341][342][343][344][345][346][347][348][349] difluorination, 350,351 fluoro-selenylation, 352 iodofluorination 353 and thiofluorination 354 of electron-deficient olefins as well as partial fluorination of conjugated dienes 355 have been devised. 356 In contrast to the electrochemical fluorination strategies, the anodic oxidation protocols involving chlorides, bromides and iodides typically proceed via generation of the corresponding electrophilic molecular counterpart (X 2 ) due to the relatively low oxidation potentials of these halogen ions.…”

Section: Anodic Halogenationmentioning

confidence: 99%

Electrochemical strategies for C–H functionalization and C–N bond formation

2018

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Conventional methods for carrying out carbon-hydrogen functionalization and carbon-nitrogen bond formation are typically conducted at elevated temperatures, and rely on expensive catalysts as well as the use of stoichiometric, and perhaps toxic, oxidants. In this regard, electrochemical synthesis has recently been recognized as a sustainable and scalable strategy for the construction of challenging carbon-carbon and carbon-heteroatom bonds. Here, electrosynthesis has proven to be an environmentally benign, highly effective and versatile platform for achieving a wide range of nonclassical bond disconnections via generation of radical intermediates under mild reaction conditions. This review provides an overview on the use of anodic electrochemical methods for expediting the development of carbon-hydrogen functionalization and carbon-nitrogen bond formation strategies. Emphasis is placed on methodology development and mechanistic insight and aims to provide inspiration for future synthetic applications in the field of electrosynthesis.

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Electrochemical iodofluorination of electron-deficient olefins

Cited by 16 publications

References 12 publications

Selective electrochemical fluorination of organic molecules and macromolecules in ionic liquids

Selective electrochemical fluorination of organic molecules and macromolecules in ionic liquids

3D Printed Reactionware for Synthetic Electrochemistry with Hydrogen Fluoride Reagents

Electrochemical strategies for C–H functionalization and C–N bond formation

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