51560-17-9Relevant articles and documents
Photocatalytic Oxidative Iodination of Electron-Rich Arenes
Narobe, Rok,Düsel, Simon J. S.,Iskra, Jernej,K?nig, Burkhard
supporting information, p. 3998 - 4004 (2019/07/17)
A visible-light-mediated oxidative iodination of electron-rich arenes has been developed. 2.5 mol% of unsubstituted anthraquinone as photocatalyst were used in combination with elementary iodine, trifluoroacetic acid and oxygen as the terminal oxidant. The iodination proceeds upon irradiation in non- or weakly-electron donating solvents (DCM, DCE and benzene) wherein a spectral window in strongly coloured iodine solutions can be observed at around 400 nm. The method provides good to excellent yields (up to 98%) and shows excellent regioselectivity and good functional group tolerance (triple bonds, ketone, ester, amide). Moreover, the photo-iodination was also upscaled to a 5 mmol scale (1.1 g). Mechanistic investigations by intermediate trapping and competition experiments indicate a photocatalytic arene oxidation and the subsequent reaction with iodine as a likely mechanistic pathway. (Figure presented.).
Method for synthesizing mono-aryl iodide or di-aryl iodide based on aromatic hydrocarbon carboxylic acid decarboxylic reaction
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Paragraph 0089; 0090, (2017/07/23)
The invention discloses a method for synthesizing mono-aryl iodide or di-aryl iodide based on aromatic hydrocarbon carboxylic acid decarboxylic reaction. The method is characterized in that under a protective atmosphere, carrying out one-pot reaction on a
Bronsted acidic ionic liquid accelerated halogenation of organic compounds with N-halosuccinimides (NXS)
Vrazic, Dejan,Jereb, Marjan,Laali, Kenneth K.,Stavber, Stojan
, p. 74 - 96 (2013/04/10)
The Bronsted-Acidic ionic liquid 1-methyl-3-(4-sulfobutyl) imidazolium triflate [BMIM(SO3H)][OTf] was demonstrated to act efficiently as solvent and catalyst for the halogenation of activated organic compounds with N-halosuccinimides (NXS) under mild conditions with short reaction times. Methyl aryl ketones were converted into a-halo and a,a-dihaloketones, depending on the quantity of NXS used. Ketones with activated aromatic rings were selectively halogenated, however in some cases mixtures of a-halogenated ketone and ring-halogenated ketones were obtained. Activated aromatics were regioselectively ring halogenated to give mono- and dihalo-substituted products. The [BMIM(SO3H)][OTf] ionic liquid (IL-A) was successfully reused eight times in a representative monohalogenation reaction with no noticeable decrease in efficiency. An effective halogenation scale-up in this IL is also presented. The reactivity trend and the observed chemo- and regioselectiivities point to an ET process in these IL-promoted halofunctionalization reactions.