90990-92-4Relevant articles and documents
Oxidatively Catalyzed Nucleophilic Aromatic Substitution. Further Studies on the SON2 Reaction
Joensson, Lennart,Wistrand, Lars-Goeran
, p. 3340 - 3344 (1984)
The oxidation of several electron-rich fluoroarenes in the presence of nucleophile, usually acetate ion, has been investigated.Two substrates, 1- and 2-fluoronaphthalene, have been shown to undergo formally nonoxidative fluorine/acetoxy exchange induced by chemical oxidants such as benzoyl peroxide, potassium peroxydisulfate, and copper(III).The mechanism is believed to involve electron-transfer chain catalysis according to the SON2 mechanism.On electrochemical oxidation of these substrates, the major pathway observed was oxidative substitution of hydrogen.The catalytic efficiency of the anodically initiated title reaction is also improved at higher temperatures; e.g., anodic acetoxydefluorination of 4-fluoroanisole takes place with a current efficiency of 590percent at 78 deg C.We also give the first example of an intramolecular although not catalytic SON2 reaction.