scholarly journals Hybrid super electron donors – preparation and reactivity

2012 ◽  
Vol 8 ◽  
pp. 994-1002 ◽  
Author(s):  
Jean Garnier ◽  
Douglas W Thomson ◽  
Shengze Zhou ◽  
Phillip I Jolly ◽  
Leonard E A Berlouis ◽  
...  
Keyword(s):  
Room Temperature ◽  
Sodium Hydride ◽  
Electron Donors ◽  
Transfer Reactions ◽  
Aryl Radical ◽  
Selective Effect ◽  
Aryl Radicals ◽  
Organic Electron ◽  
Show Evidence ◽  
Excess Sodium

Neutral organic electron donors, featuring pyridinylidene–imidazolylidene, pyridinylidene–benzimidazolylidene and imidazolylidene–benzimidazolylidene linkages are reported. The pyridinylidene–benzimidazolylidene and imidazolylidene–benzimidazolylidene hybrid systems were designed to be the first super electron donors to convert iodoarenes to aryl radicals at room temperature, and indeed both show evidence for significant aryl radical formation at room temperature. The stronger pyridinylidene–imidazolylidene donor converts iodoarenes to aryl anions efficiently under appropriate conditions (3 equiv of donor). The presence of excess sodium hydride base has a very important and selective effect on some of these electron-transfer reactions, and a rationale for this is proposed.

Ground State Cross-Coupling of Haloarenes with Arenes Initiated by Organic Electron Donors, Formed in situ: An Overview

Synthesis ◽  
2019 ◽  
Vol 52 (03) ◽  
pp. 327-336 ◽  
Author(s):  
Giuseppe Nocera ◽  
John A. Murphy
Keyword(s):  
Coupling Reaction ◽  
Organic Additive ◽  
Electron Donors ◽  
Aromatic Substitution ◽  
Organic Additives ◽  
Aryl Radical ◽  
Wide Range ◽  
Homolytic Aromatic Substitution ◽  
Organic Electron

Many reactions have been discovered that lead to coupling of haloarenes to arenes using potassium tert-butoxide as the base, and one of a variety of organic compounds as an additive. The organic additive reacts with the base to form a strong organic electron donor in situ that initiates a base-induced homolytic aromatic substitution (BHAS) coupling reaction, by converting the haloarene into an aryl radical. This brief report presents an overview of the wide range of organic additives that can be used, and the organic electron donors that they form.

Switching from single to simultaneous free radical and anionic polymerization with enamine‐based organic electron donors

2021 ◽  
Author(s):  
Yuxi Zhao ◽  
Marion Rollet ◽  
Laurence Charles ◽  
Gabriel Canard ◽  
Didier Gigmes ◽  
...  
Keyword(s):  
Free Radical ◽  
Anionic Polymerization ◽  
Electron Donors ◽  
Organic Electron

σ-Bond initiated generation of aryl radicals from aryl diazonium salts

2020 ◽  
Vol 18 (9) ◽  
pp. 1812-1819 ◽  
Author(s):  
Elene Tatunashvili ◽  
Bun Chan ◽  
Philippe E. Nashar ◽  
Christopher S. P. McErlean
Keyword(s):  
Room Temperature ◽  
Radical Reactions ◽  
Diazonium Salts ◽  
Aryl Radicals

Hantzsch esters and oxygen convert diazonium salts into aryl radicals, enabling rapid radical reactions to be performed in open flasks at room temperature.

scholarly journals A combined experimental and theoretical study on the reactivity of nitrenes and nitrene radical anions

2022 ◽  
Vol 13 (1) ◽  
Author(s):  
Yujing Guo ◽  
Chao Pei ◽  
Rene M. Koenigs
Keyword(s):  
Radical Anion ◽  
Room Temperature ◽  
Theoretical Study ◽  
Transition Metal Catalysts ◽  
Transfer Reactions ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Nitrene Transfer ◽  
Triplet Nitrene ◽  
Nitrogen Bonds

AbstractNitrene transfer reactions represent one of the key reactions to rapidly construct new carbon-nitrogen bonds and typically require transition metal catalysts to control the reactivity of the pivotal nitrene intermediate. Herein, we report on the application of iminoiodinanes in amination reactions under visible light photochemical conditions. While a triplet nitrene can be accessed under catalyst-free conditions, the use of a suitable photosensitizer allows the access of a nitrene radical anion. Computational and mechanistic studies rationalize the access and reactivity of triplet nitrene and nitrene radical anion and allow the direct comparison of both amination reagents. We conclude with applications of both reagents in organic synthesis and showcase their reactivity in the reaction with olefins, which underline their markedly distinct reactivity. Both reagents can be accessed under mild reaction conditions at room temperature without the necessity to exclude moisture or air, which renders these metal-free, photochemical amination reactions highly practical.

Graftfast©: Towards the Control of Surface Properties of any Type of Materials by the Grafting of Polymers

2012 ◽  
Vol 445 ◽  
pp. 797-802 ◽  
Author(s):  
Alice Mesnage ◽  
Pardis Simon ◽  
Guy Deniau ◽  
Nathalie Herlin-Boime ◽  
Serge Palacin
Keyword(s):  
Surface Properties ◽  
Polymer Films ◽  
Atmospheric Pressure ◽  
Room Temperature ◽  
Diazonium Salts ◽  
Green Process ◽  
Graft Polymer ◽  
Grafted Polymer ◽  
Aryl Radicals ◽  
One Step

This document aims at presenting and explaining the mechanism of a simple green process, called Graftfast©, recently developed in order to graft polymer films onto any type of materials. This process is of great interest as it works in a short one step reaction at room temperature, atmospheric pressure in water. Particularly since this method is a redoxinduced process consisting in the reduction of diazonium salts into aryl radicals in presence of vinylic monomer, the involvement of such radicals was investigated. Moreover, this work demonstrates the efficiency of such process for the preparation of functionalized TiO2 nanoparticles. The composition and the grafted polymer quantities were investigated showing the successful grafting of the polymer onto the nanoparticles while conserving their morphology.

Convenient new synthesis of 1,3-diaroylureas

1969 ◽  
Vol 47 (11) ◽  
pp. 2097-2099 ◽  
Author(s):  
James F. Wolfe ◽  
George B. Trimitsis
Keyword(s):  
Sodium Hydride ◽  
Aromatic Esters ◽  
New Synthesis ◽  
Excess Sodium

It has been found that symmetrical 1,3-diaroylureas can be prepared in good yields by allowing urea to react with aromatic esters and excess sodium hydride in refluxing 1,2-dimethoxyethane. Applications of this method to the synthesis of unsymmetrical 1,3-diaroylureas and substituted monoaroylureas are also described.

scholarly journals Base-Free Generation of Organic Electron Donors from Air-Stable Precursors

2018 ◽  
Vol 57 (12) ◽  
pp. 3148-3153 ◽  
Author(s):  
Guillaume Tintori ◽  
Pierre Nabokoff ◽  
Ruqaya Buhaibeh ◽  
David Bergé-Lefranc ◽  
Sébastien Redon ◽  
...  
Keyword(s):  
Electron Donors ◽  
Organic Electron ◽  
Free Generation

Chemical reduction of Ag+ to Ag employing organic electron donors: evaluation of the effect of Ag+-mediated cytosine–cytosine base pairing on the aggregation of Ag nanoparticles

2021 ◽  
Author(s):  
Takenori Dairaku ◽  
Rika Kawai ◽  
Kanako Nozawa-Kumada ◽  
Kentaro Yoshida ◽  
Tetsuya Ono ◽  
...  
Keyword(s):  
Ag Nanoparticles ◽  
Chemical Reduction ◽  
Total Concentration ◽  
Electron Donors ◽  
Base Pairing ◽  
Reduction Activity ◽  
Organic Electron

The formation of C–Ag+–C base pairing inhibits the aggregation of AgNPs in solution. The total concentration of the obtained AgNP solution can be controlled by the degree of the reduction activity of the organic electron donors.

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