129-81-7Relevant articles and documents
α-Iodination of enaminones with bis(pyridine)iodonium(I) tetrafluoroborate
Campos, Pedro J.,Arranz, Joaquin,Rodriguez, Miguel A.
, p. 8397 - 8400 (1997)
Primary, secondary and tertiary enaminones react with bis(pyridine)iodonium(I) tetrafluoroborate in methylene chloride at room temperature to give α-iodo enaminones in almost quantitative yields. The reported reaction is the fast known example of direct iodination of tertiary enaminones.
Reactivity of antipyrine and haloantipyrines in Pd-catalyzed C–H bond arylations
Bera, Jitendra K.,Doucet, Henri,Sasmal, Arpan,Soulé, Jean-Fran?ois
, (2020)
We reported herein the Pd-catalyzed direct arylation of antipyrine using Pd(OAc)2 as catalyst associated with KOAc as inexpensive base. In most cases, diethyl carbonate was used a sustainable solvent. The reaction tolerated a wide range of functional groups on the aryl bromide partners (e.g., nitrile, nitro, chloro, fluoro, formyl, acetyl, propionyl, benzoyl, ester, methyl, methoxy). In addition, some nitrogen-containing heteroaryl bromides were also efficiently coupled with antipyrine. We also demonstrated that in contrast to 4-bromoantipyrine, 4-iodoantipyrine could be employed as an efficient heteroaryl source in Pd-catalyzed C–H bond arylation of 5-membered ring heteroarenes.
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.).
Metallation of heteroaryls and its application to isotopic labelling
Allen, Paul H.,Coissard, Vincent,Hickey, Michael J.,Hogg, Colin,Kingston, Lee P.,Caffrey, Moya,Wilkinson, David J.
experimental part, p. 81 - 84 (2010/09/14)
The recently published procedure for the metallation of heteroaromatics and their subsequent reaction with iodine has been applied to the synthesis of deuterium-labelled compounds. The mixed magnesium/lithium base (2) has been prepared and reacted with a range of heteroaromatics. The metallated compounds were iodolyzed with molecular iodine and the resulting iodo compounds were reductively dehalogenated with deuterium gas. This allowed confirmation of the regiochemistry of the metallation and the use of the procedure as a labelling method. Copyright
