scholarly journals Aryl radical-mediated N-heterocyclic carbene catalysis

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yuki Matsuki ◽  
Nagisa Ohnishi ◽  
Yuki Kakeno ◽  
Shunsuke Takemoto ◽  
Takuya Ishii ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Single Electron ◽  
Radical Reactions ◽  
Single Electron Transfer ◽  
Aryl Radical ◽  
Aryl Iodide ◽  
Alkyl Radicals ◽  
Aryl Radicals ◽  
Electron Transfer Processes ◽  
Secondary Amides

AbstractThere have been significant advancements in radical reactions using organocatalysts in modern organic synthesis. Recently, NHC-catalyzed radical reactions initiated by single electron transfer processes have been actively studied. However, the reported examples have been limited to catalysis mediated by alkyl radicals. In this article, the NHC organocatalysis mediated by aryl radicals has been achieved. The enolate form of the Breslow intermediate derived from an aldehyde and thiazolium-type NHC in the presence of a base undergoes single electron transfer to an aryl iodide, providing an aryl radical. The catalytically generated aryl radical could be exploited as an arylating reagent for radical relay-type arylacylation of styrenes and as a hydrogen atom abstraction reagent for α-amino C(sp3)–H acylation of secondary amides.

scholarly journals Alcohol-Initiated Dediazoniation of Aryldiazonium Ions to Aryl Radicals: A Simple and Efficient Route to Arylboronates

2018 ◽  
Vol 42 (9) ◽  
pp. 481-485
Author(s):  
Xiulian Zhang ◽  
Zhicheng Zhang ◽  
Yongbin Xie ◽  
Yujie Jiang ◽  
Ruibo Xu ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Bond Formation ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Aryl Radical ◽  
Radical Species ◽  
Aryl Radicals ◽  
Efficient Access ◽  
Efficient Route ◽  
Operational Simplicity

A simple and efficient access to arylboronates was achieved with methanol-initiated borylation of aryldiazonium salts. Reduction of aryldiazonium ions by single electron transfer from methanol affords aryl radical species, which undergo a subsequent C–B bond formation with bis(pinacolato)diboron. This highly practical borylation process, which can be carried out on the gram-scale, enjoys operational simplicity as well as mild and catalyst-free conditions.

scholarly journals Cascades, Catalysis and Chiral Ligand Control with SmI2; The Rebirth of a Reagent

2020 ◽  
Vol 74 (1) ◽  
pp. 18-22
Author(s):  
Áron Péter ◽  
David J. Procter
Keyword(s):  
Electron Transfer ◽  
Cascade Reactions ◽  
Single Electron ◽  
Radical Reactions ◽  
Chiral Ligand ◽  
Single Electron Transfer ◽  
Recent Developments ◽  
Radical Cascade

This review focuses on recent developments from our laboratory in the field of radical reactions mediated by the archetypal reductive single electron transfer (SET) reagent, SmI2. Namely, we have expanded the scope of reducible carbonyl moieties to esters and amides and have exploited the resultant ketyl radicals in radical cascade reactions that generate unprecedented scaffolds. Moreover, we have taken the first steps to address the long-standing challenges of catalysis and chiral ligand control associated with the reagent.

scholarly journals Intermolecular oxyarylation of olefins with aryl halides and TEMPOH catalyzed by the phenolate anion under visible light

2020 ◽  
Vol 11 (27) ◽  
pp. 6996-7002
Author(s):  
Kangjiang Liang ◽  
Qian Liu ◽  
Lei Shen ◽  
Xipan Li ◽  
Delian Wei ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Visible Light ◽  
Aryl Halides ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Strong Reduction ◽  
Aryl Radicals ◽  
Reduction Potentials

The phenolate anion was developed as a new photocatalyst with strong reduction potentials (−3.16 V vs. SCE) to reduction of aryl halides to aryl radicals through single electron transfer.

scholarly journals Chiral Nitroarenes as Enantioselective Single-Electron-Transfer Oxidants for Carbene-Catalyzed Radical Reactions

2019 ◽  
Vol 21 (18) ◽  
pp. 7440-7444 ◽  
Author(s):  
Hongling Wang ◽  
Yuhuang Wang ◽  
Xingkuan Chen ◽  
Chengli Mou ◽  
Shuyan Yu ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Single Electron ◽  
Radical Reactions ◽  
Single Electron Transfer

scholarly journals Synthesis of indanes via carbene-catalyzed single-electron-transfer processes and cascade reactions

2017 ◽  
Vol 53 (87) ◽  
pp. 11952-11955 ◽  
Author(s):  
Yuhuang Wang ◽  
Xingxing Wu ◽  
Yonggui Robin Chi
Keyword(s):  
Electron Transfer ◽  
Michael Addition ◽  
Cascade Reactions ◽  
Cascade Reaction ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Transfer Processes ◽  
Electron Transfer Processes

An NHC-catalyzed cascade reaction involving an SET process and two sequential Michael addition steps for the synthesis of indanes is disclosed.

Cyclic voltammetry of diphenylpicrylhydrazyl in tetrahydrofuran

1968 ◽  
Vol 46 (8) ◽  
pp. 1337-1340 ◽  
Author(s):  
B. Lionel Funt ◽  
Derek G. Gray
Keyword(s):  
Electron Transfer ◽  
Cyclic Voltammetry ◽  
Free Radical ◽  
Anionic Polymerization ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Transfer Processes ◽  
Suitable Medium ◽  
The Stability ◽  
Electron Transfer Processes

Cyclic voltammetry has revealed four reversible single electron transfer processes in the oxidation and reduction of diphenylpicrylhydrazyl (DPPH) in tetrahydrofuran (THF). These are associated with a cation, a free radical, a monoanion, a dianion radical, and a trianion of DPPH.THF is a good solvent for cyclic voltammetry as evidenced by the stability of the products generated at the electrodes. It is also one of the few excellent solvents for anionic polymerization and is therefore a remarkably suitable medium for studies of electropolymerization phenomena.

Palladium-mediated radical homocoupling reactions: a surface catalytic insight

2018 ◽  
Vol 8 (18) ◽  
pp. 4766-4773 ◽  
Author(s):  
Isabelle Favier ◽  
Marie-Lou Toro ◽  
Pierre Lecante ◽  
Daniel Pla ◽  
Montserrat Gómez
Keyword(s):  
Electron Transfer ◽  
Metal Surface ◽  
Functional Group ◽  
Single Electron ◽  
Mechanistic Study ◽  
Single Electron Transfer ◽  
Palladium Nanoparticle ◽  
Transfer Processes ◽  
Electron Transfer Processes ◽  
Reductive Homocoupling

In this work, we report a palladium nanoparticle-promoted reductive homocoupling of haloarenes, exhibiting a broad functional group tolerance. A mechanistic study was carried out, suggesting single-electron transfer processes on the metal surface.

scholarly journals Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): Efficient formation of products derived from aryl radicals

2009 ◽  
Vol 5 ◽  
Author(s):  
Mohan Mahesh ◽  
John A Murphy ◽  
Franck LeStrat ◽  
Hans Peter Wessel
Keyword(s):  
Electron Transfer ◽  
Radical Cyclizations ◽  
Single Electron Transfer ◽  
Aryl Radical ◽  
Relative Ease ◽  
Aryl Radicals ◽  
Radical Intermediates ◽  
Arenediazonium Salts ◽  
First Time ◽  
By Products

Tetrakis(dimethylamino)ethylene (TDAE 1), has been exploited for the first time as a mild reagent for the reduction of arenediazonium salts to aryl radical intermediates through a single electron transfer (SET) pathway. Cyclization of the aryl radicals produced in this way led, in appropriate substrates, to syntheses of indolines and indoles. Cascade radical cyclizations of aryl radicals derived from arenediazonium salts are also reported. The relative ease of removal of the oxidized by-products of TDAE from the reaction mixture makes the methodology synthetically attractive.

A novel samarium(ii) complex bearing a dianionic bis(phenolate) cyclam ligand: synthesis, structure and electron-transfer reactions

2016 ◽  
Vol 45 (9) ◽  
pp. 3778-3790 ◽  
Author(s):  
Leonor Maria ◽  
Marina Soares ◽  
Isabel C. Santos ◽  
Vânia R. Sousa ◽  
Elsa Mora ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Single Electron ◽  
Transfer Reactions ◽  
Single Electron Transfer ◽  
Electron Transfer Reactions ◽  
Transfer Processes ◽  
Highly Effective ◽  
Samarium Complex ◽  
Ligand Synthesis ◽  
Electron Transfer Processes

A novel divalent samarium complex anchored on a dianionic bis(phenolate) ligand is reported and reactivity studies demonstrate that it is highly effective in inducing single-electron transfer processes.

Sign in / Sign up

Export Citation Format

Share Document