Microwave role in the thermally induced SRN1 reaction for α-arylation of ketones

RSC Advances ◽  
2015 ◽  
Vol 5 (26) ◽  
pp. 20058-20065 ◽  
Author(s):  
Daniel A. Caminos ◽  
Alexis D. Garro ◽  
Silvia M. Soria-Castro ◽  
Alicia B. Peñéñory
Keyword(s):  
Electron Transfer ◽  
Microwave Irradiation ◽  
Nucleophilic Substitution ◽  
Transfer Mechanism ◽  
Electron Transfer Mechanism ◽  
Thermally Induced ◽  
Srn1 Reaction

Microwave irradiation promotes nucleophilic substitution by thermally induced electron transfer mechanism.

scholarly journals An expedient route to heterocycles through α-arylation of ketones and arylamides by microwave induced thermal SRN1 reactions

RSC Advances ◽  
2014 ◽  
Vol 4 (34) ◽  
pp. 17490-17497 ◽  
Author(s):  
Silvia M. Soria-Castro ◽  
Daniel A. Caminos ◽  
Alicia B. Peñéñory
Keyword(s):  
Electron Transfer ◽  
Microwave Irradiation ◽  
Nucleophilic Substitution ◽  
Transfer Mechanism ◽  
Ring Closure ◽  
Electron Transfer Mechanism ◽  
Thermally Induced ◽  
Intramolecular Ring

Quick reaction by microwave irradiation promotes nucleophilic substitution by thermally induced electron transfer mechanism and allows to synthesize deoxibenzoin and indol heterocycles derivates by inter or intramolecular ring closure.

Electron transfer mechanism of aromatic 'nucleophilic' substitution

1972 ◽  
Vol 25 (10) ◽  
pp. 2133 ◽  
Author(s):  
PR Singh ◽  
R Kumar
Keyword(s):  
Electron Transfer ◽  
Nucleophilic Substitution ◽  
Potassium Iodide ◽  
Transfer Mechanism ◽  
Salt Solutions ◽  
Aromatic Nucleophilic Substitution ◽  
Electron Transfer Mechanism ◽  
Heterolytic Cleavage ◽  
Radical Intermediates ◽  
Photochemical Catalysis

Mechanistic implications of the ready formation of aryl iodides from aryldiazonium salt solutions and the iodide ion (in contrast with the general need for cuprous or other catalysts with other halides) have been studied. The reaction between benzenediazonium fluoroborate and potassium iodide in methanol at 0�C has been investigated. A new mechanism involving initial one-electron transfer from the iodide anion to the benzenediazonium cation, resulting in the formation of radical intermediates by heterolytic cleavage of a bond, has been proposed in order to account for the products, viz. iodobenzene, benzene, biphenyl, iodine, anisole, and formaldehyde, and the effect of photochemical catalysis.

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