Arylation of aromatic compounds by electrochemical reduction of benzenediazonium tetrafluoroborate in aprotic solvents

Gadallah, F. F.; Elofson, R. M.

doi:10.1021/jo01263a025

Cited by 40 publications

(20 citation statements)

References 1 publication

(1 reference statement)

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“…Figure S3 shows the absorbance of the diazonium salt which does not significantly change in the presence of DNA (the slight absorbance decrease is mainly due to its instability in water): this strongly suggest no reactivity of the salt with DNA. The exclusive reactivity of diazonium salts with SWCNTs exists because of an electron is transferred from the nanotube to the diazonium functionality, releasing N 2 and forming a reactive aryl radical which further reacts with the carbon nanotube; it is possible to produce the same radical electrolytically reducing diazonium salts …”

Section: Figurementioning

confidence: 99%

A One‐Step Chemical Strategy for the Formation of Carbon Nanotube Junctions in Aqueous Solution: Reaction of DNA‐Wrapped Carbon Nanotubes with Diazonium Salts

et al. 2019

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A single‐step chemical strategy allows the formation of single‐walled carbon nanotube (SWCNT) molecular junctions in aqueous solution. SWCNTs were first wrapped with DNA to be water soluble and solution processable. Diazonium salts, which have been shown to react spontaneously with carbon nanotubes in water at room temperature, were then employed to covalently link SWCNT segments. The DNA wrapping of the nanotubes acted as a protective layer that limits the functionalization predominantly to the nanotube terminal ends, therefore allowing the assembly of linear SWCNT junctions. Upon increasing the concentration of the linker, we observed first the formation of side‐to‐end junctions, and eventually the assembly, through side‐to‐side interactions, of SWCNTs into bundles. This approach demonstrates the possibility of tuning the formation of linear and branched carbon nanotube junctions that in turn is of importance for the sustainable fabrication of solution‐processable CNT‐based nanoscale systems and devices.

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Section: Figurementioning

confidence: 99%

A One‐Step Chemical Strategy for the Formation of Carbon Nanotube Junctions in Aqueous Solution: Reaction of DNA‐Wrapped Carbon Nanotubes with Diazonium Salts

et al. 2019

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“…2 2 9~ + 0.314) V vs. sce These findings led to electrochemical techniques for arylations (2) and Pschorr reactions (3). The positive reduction potentials agree well with the strong electrophilicity of diazotized aromatic amines (4).…”

Section: Introductionmentioning

confidence: 64%

“…This can hardly be true for the series of aldehydes, nitro compounds, and diazonium salts -1 as described in Fig. 1, which would be expected to obey the Born equation (8) [2] where the symbols…”

Section: Discussion -3mentioning

confidence: 99%

Polarographic redox potentials of diazotized polycyclic aromatic amines and the absolute electrode potentials

Elofson¹,

Gadallah²,

Schulz³

et al. 1984

Can. J. Chem.

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Can. J. Chem. 62,1772(1984. The half-wave potentials (El/z) of polycyclic diazonium salts as well as those of the parent hydrocarbons, the corresponding aldehydes, and the nitro compounds, when plotted against the coefficient of the energy of either the lowest vacant orbital [Traduit par le journa(] Introduction In 1969, we reported the results of our work on the effect of substituents on the half-wave reduction potentials of aryl diazonium tetrafluoroborates in the aprotic solvent sulfolane (1). These results produced a good Hammett plot [l]. Only one reversible, one electron-reduction wave was observed.

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“…Electron-withdrawing substituents on the aryl moiety increase the redox potential of diazonium salts, favouring thereby, the homolytic C À N bond cleavage. Electrochemical, [37] photo-induced [38] and metal-catalyzed reductions are the main pathways for generating aryl radicals from diazonium salts. The role of the counterion in the redox process has not been rationalized nor thoroughly studied although one can expect that it does not act as a spectator regarding the reaction outcome.…”

Section: Arenediazonium Saltsmentioning

confidence: 99%

Transition Metal‐Mediated Direct CH Arylation of Heteroarenes Involving Aryl Radicals

2014

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This review gives an overview of the generation of aryl radicals, mediated by transition metals, and their use for the C À H arylation of heteroarenes. The different sources of aromatic derivatives able to generate aryl radicals via a metal-assisted reduction or oxidation are discussed, with a critical view of the developed systems. The radical arylations of nitrogen-, oxygen-or sulfur-containing heterocycles are then described and mechanistic considerations are discussed as well.

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Arylation of aromatic compounds by electrochemical reduction of benzenediazonium tetrafluoroborate in aprotic solvents

Cited by 40 publications

References 1 publication

A One‐Step Chemical Strategy for the Formation of Carbon Nanotube Junctions in Aqueous Solution: Reaction of DNA‐Wrapped Carbon Nanotubes with Diazonium Salts

A One‐Step Chemical Strategy for the Formation of Carbon Nanotube Junctions in Aqueous Solution: Reaction of DNA‐Wrapped Carbon Nanotubes with Diazonium Salts

Polarographic redox potentials of diazotized polycyclic aromatic amines and the absolute electrode potentials

Transition Metal‐Mediated Direct CH Arylation of Heteroarenes Involving Aryl Radicals

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