Reduction by a model of NAD(P)H. 45. Mechanism for the dediazoniation of arenediazonium salts initiated by one-electron transfer from an NAD(P)H model

1984 ◽  
Vol 49 (5) ◽  
pp. 878-882 ◽  
Author(s):  
Shinro Yasui ◽  
Kaoru Nakamura ◽  
Atsuyoshi Ohno
Keyword(s):  
Electron Transfer ◽  
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.

ChemInform Abstract: Electron Transfer Between Hemoglobin and Arenediazonium Salts. Mechanism of Heme Aryl-Iron Complex Formation.

ChemInform ◽  
1988 ◽  
Vol 19 (4) ◽  
Author(s):  
M. P. DOYLE ◽  
S. N. MAHAPATRO ◽  
J. K. GUY ◽  
M. R. HESTER ◽  
C. M. VAN ZYL ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Complex Formation ◽  
Iron Complex ◽  
Arenediazonium Salts

Aromatic substitutions of arenediazonium salts via metal catalysis, single electron transfer, and weak base mediation

2018 ◽  
Vol 16 (27) ◽  
pp. 4942-4953 ◽  
Author(s):  
Denis Koziakov ◽  
Guojiao Wu ◽  
Axel Jacobi von Wangelin
Keyword(s):  
Electron Transfer ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Weak Base ◽  
Metal Catalysis ◽  
Hazard Potential ◽  
Recent Developments ◽  
Arenediazonium Salts ◽  
Operational Simplicity

Radical aromatic substitutions of arenediazonium salts can be initiated by various methods. The recent developments of weak base-mediated protocols provide great advantages over conventional metal-mediated or photoredox reactions by their operational simplicity, price, hazard potential and scalability.

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