Aryl Radical Formation by Copper(I) Photocatalyzed Reduction of Diaryliodonium Salts: NMR Evidence for a CuII/CuIMechanism

2013 ◽  
Vol 19 (33) ◽  
pp. 10809-10813 ◽  
Author(s):  
Alexandre Baralle ◽  
Louis Fensterbank ◽  
Jean-Philippe Goddard ◽  
Cyril Ollivier
Keyword(s):  
Radical Formation ◽  
Aryl Radical ◽  
Diaryliodonium Salts

Halogen bonding matters: visible light-induced photoredox catalyst-free aryl radical formation and its applications

2020 ◽  
Vol 22 (18) ◽  
pp. 10212-10218 ◽  
Author(s):  
Rong Miao ◽  
Dan Wang ◽  
Jianliang Xiao ◽  
Jiani Ma ◽  
Dong Xue ◽  
...  
Keyword(s):  
Visible Light ◽  
Aryl Halide ◽  
Halogen Bonding ◽  
Radical Formation ◽  
Aryl Radical ◽  
Catalyst Free ◽  
Visible Light Driven

Halogen bonding facilitated aryl halide activation for photoredox catalyst-free visible light-driven reactions.

scholarly journals Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals

2017 ◽  
Vol 8 (5) ◽  
pp. 3618-3622 ◽  
Author(s):  
L. Candish ◽  
M. Freitag ◽  
T. Gensch ◽  
F. Glorius
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Radical Formation ◽  
Photoredox Catalysis ◽  
Aryl Radical ◽  
Aryl Radicals

Herein we present the first example of aryl radical formation via the visible light-mediated decarboxylation of aryl carboxylic acids using photoredox catalysis.

Radical C‒N Borylation of Aromatic Amines Enabled by a Pyrylium Reagent

2019 ◽  
Author(s):  
Yuanhong Ma ◽  
Yue Pang ◽  
jan niski ◽  
Markus Leutzsch ◽  
Josep Cornella
Keyword(s):  
Aromatic Amines ◽  
Driving Force ◽  
Bond Cleavage ◽  
Radical Reaction ◽  
Radical Formation ◽  
Planar Structure ◽  
Amino Group ◽  
Aryl Radical ◽  
Electronic Environment

Herein, we report a radical borylation of aromatic amines through a homolytic C(sp2)‒N bond cleavage. This method capitalizes on a simple and mild activation via a pyrylium reagent (ScPyry-OTf) thus priming the amino group for reactivity. The combination of terpyridine and a diboron reagent triggers a radical reaction which cleaves the C(sp2)‒N bond and forges a new C(sp2)‒B bond. The unique non-planar structure of the pyridinium intermediate, provides the necessary driving force for the aryl radical formation. The method permits borylation of a wide variety of aromatic amines indistinctively of the electronic environment.<br>

scholarly journals Radical C‒N Borylation of Aromatic Amines Enabled by a Pyrylium Reagent

2019 ◽  
Author(s):  
Yuanhong Ma ◽  
Yue Pang ◽  
jan niski ◽  
Markus Leutzsch ◽  
Josep Cornella
Keyword(s):  
Aromatic Amines ◽  
Driving Force ◽  
Bond Cleavage ◽  
Radical Reaction ◽  
Radical Formation ◽  
Planar Structure ◽  
Amino Group ◽  
Aryl Radical ◽  
Electronic Environment

Herein, we report a radical borylation of aromatic amines through a homolytic C(sp2)‒N bond cleavage. This method capitalizes on a simple and mild activation via a pyrylium reagent (ScPyry-OTf) thus priming the amino group for reactivity. The combination of terpyridine and a diboron reagent triggers a radical reaction which cleaves the C(sp2)‒N bond and forges a new C(sp2)‒B bond. The unique non-planar structure of the pyridinium intermediate, provides the necessary driving force for the aryl radical formation. The method permits borylation of a wide variety of aromatic amines indistinctively of the electronic environment.<br>

Combining Electrochemistry and Computational Chemistry to Understand Aryl-Radical Formation in Electrografting Processes

2018 ◽  
Vol 95 (8) ◽  
pp. 1386-1391 ◽  
Author(s):  
Miriam C. Rodríguez González ◽  
Alberto Hernández Creus ◽  
Pilar Carro
Keyword(s):  
Computational Chemistry ◽  
Radical Formation ◽  
Aryl Radical

Aryl Radical Formation during the Metabolism of Arylhydrazines by Microsomes

1997 ◽  
Vol 10 (12) ◽  
pp. 1372-1377 ◽  
Author(s):  
Peter M. Gannett ◽  
Xiangling Shi ◽  
Terence Lawson ◽  
Carol Kolar ◽  
Bela Toth
Keyword(s):  
Radical Formation ◽  
Aryl Radical

Aryl radical-induced desulfonylative ipso-substitution of diaryliodonium salts: an efficient route to sterically hindered biarylamines

2020 ◽  
Vol 56 (42) ◽  
pp. 5697-5700 ◽  
Author(s):  
Huangguan Chen ◽  
Limin Wang ◽  
Jianwei Han
Keyword(s):  
Reaction Pathway ◽  
Aryl Radical ◽  
Ipso Substitution ◽  
Diaryliodonium Salts ◽  
Efficient Route ◽  
Sterically Hindered ◽  
Induced Reaction

By using vicinal aryl sulfonamide-substituted diaryliodonium salts, a cascade of desulfonylation/aryl migration was promoted by triethylamine in synthesis of sterically hindered biarylamines, which operated via a radical-induced reaction pathway.

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