Reduction of Arenediazonium Salts by Tetrakis(Dimethylamino) Ethylene (TDAE): Efficient Formation of Products Derived from Aryl Radicals

2011 ◽  
pp. 347-365
Keyword(s):  
Aryl Radicals ◽  
Arenediazonium Salts

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.

The Intermediacy of Free Aryl Radicals in the Reaction of o-Alkenyloxybenzenediazonium Salts With Ferrocene

1992 ◽  
Vol 45 (5) ◽  
pp. 857 ◽  
Author(s):  
ALJ Beckwith ◽  
RA Jackson ◽  
RW Longmore
Keyword(s):  
Electron Transfer ◽  
Aryl Radicals ◽  
Arenediazonium Salts

The formation of 3-ferrocenylmethyl-2,3-dihydrobenzofuran (5a) and similar products bearing cyclized substituents, when ferrocene or mixtures of ferrocene and ferrocenium ion are treated witho - allyloxybenzene - or o-but-3-enyloxybenzene-dimonium salts, provides unequivocal evidence for the intermediacy of free aryl radicals in the reaction of ferrocene with arenediazonium salts. The results are consistent with a mechanism involving electron transfer and dediazoniation followed by homolytic attack on ferroce nium ion.

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.

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