709-49-9Relevant academic research and scientific papers
An efficient gram scale synthesis of aryl iodides from aryl diazofluoroborates in water under mild conditions
Gholap, Somnath S.
, p. 594 - 599 (2018/06/26)
Transition metal-free synthesis of synthetically valuable aryl iodides from aryl diazofluroborates in water under mild conditions has been described. Majority of synthesized aryl iodides are obtained in quantitative yields (>99%) under present reaction conditions. The structural effects due to the substituents present on aryl diazofluoroborates did not show any satisfactory effect on the yields of the aryl iodides. Hence, the methodology presented here was found to be adventitious for the quantitative production of synthetically valuable aryl iodides.
Late stage iodination of biologically active agents using a one-pot process from aryl amines
Sloan, Nikki L.,Luthra, Sajinder K.,McRobbie, Graeme,Pimlott, Sally L.,Sutherland, Andrew
, p. 54881 - 54891 (2017/12/12)
A simple and effective one-pot tandem procedure that generates aryl iodides from readily available aryl amines via stable diazonium salts has been developed. The operationally simple procedure and mild conditions allow late-stage iodination of a wide range of aryl compounds bearing various functional groups and substitution patterns. A novel synthetic strategy involving the preparation of nitroaryl compounds followed by a chemoselective tin(ii) dichloride reduction and the use of the one-pot diazotisation-iodination transformation was also developed. The general applicability of this approach was demonstrated with the preparation of a number of medicinally important compounds including CNS1261, a SPECT imaging agent of the N-methyl-d-aspartate (NMDA) receptor and IBOX, a compound used to detect amyloid plaques in the brain.
Acidic ionic liquid supported on silica-coated magnetite nanoparticles as a green catalyst for one-pot diazotization-halogenation of the aromatic amines
Isaad, Jalal
, p. 49333 - 49341 (2014/12/10)
Acidic ionic liquid was immobilized on silica-coated magnetite nanoparticles (Fe3O4@SILnP) and used as an efficient heterogeneous catalyst for the diazotization-iodination reaction of different aromatic amines under solvent-free conditions at room temperature. The diazonium salts that are formed by this catalyst are stable at room temperature and react rapidly with sodium iodide to produce aryl iodides in good to excellent yields. This method has some advantages such as low pollution, rapid access to products, simple work-up and easy separation of catalyst from the reaction mixture.
A one-pot method for the iodination of aryl amines via stable aryl diazonium silica sulfates under solvent-free conditions
Zarei, Amin,Hajipour, Abdol R.,Khazdoozd, Leila
experimental part, p. 941 - 944 (2009/12/02)
A convenient and rapid one-pot method for the synthesis of iodoarenes is developed which involves the sequential diazotization-iodination of aromatic amines with sodium nitrite, silica sulfuric acid and potassium iodide under solvent-free conditions at room temperature. Various aromatic amines possessing electron-withdrawing groups or electron-donating groups are converted into the corresponding aryl iodides in good yields. Georg Thieme Verlag Stuttgart.
Iodination of aryl amines in a water-paste form via stable aryl diazonium tosylates
Gorlushko, Dmitry A.,Filimonov, Victor D.,Krasnokutskaya, Elena A.,Semenischeva, Nadya I.,Go, Bong Seong,Hwang, Ho Yun,Cha, Eun Hye,Chi, Ki-Whan
, p. 1080 - 1082 (2008/09/18)
The diazotization of aryl amines at room temperature in paste form with NaNO2, p-TsOH and a small amount of water, followed by treatment with KI provides a new, simple, and effective route for the preparation of various aryl iodides. The water-paste and strong acid-free reaction conditions are environmentally friendly and compatible with acid-sensitive functional groups.
A new, one-step, effective protocol for the iodination of aromatic and heterocyclic compounds via aprotic diazotization of amines
Krasnokutskaya, Elena A.,Semenischeva, Nadya I.,Filimonov, Victor D.,Knochel, Paul
, p. 81 - 84 (2008/01/03)
We have developed a convenient one-step preparation of aromatic and some heterocyclic iodides by the sequential diazotization-iodination of the aromatic amines with a KI/NaNO2/p-TsOH system in acetonitrile at room temperature. This method has general character and allows aryl iodides with either donor or acceptor substituents in various positions to be obtained from the corresponding amines in 50-90% yield. Georg Thieme Verlag Stuttgart.
Perfluoroalkylated 4,13-diaza-18-crown-6 ethers: Synthesis, phase-transfer catalysis, and recycling studies
Stuart, Alison M.,Vidal, Jose A.
, p. 3735 - 3740 (2008/02/03)
(Chemical Equation Presented) A series of N,N′-dialkyl-4,13-diaza-18- crown-6 lariat ethers possessing two C8H17 (2), (CH 2)3C8F17 (3), (CH2) 3C10F21 (4), and (CH2) 2C8F17 (5) side arms were synthesized in good yields by N-alkylation of 4,13-diaza-18-crown-6. Potassium picrate could be extracted from an aqueous solution into an organic phase by all of the perfluoroalkylated macrocycles demonstrating their potential to be used as phase-transfer catalysts, and preliminary studies on a classical nucleophilic substitution established that they each gave higher catalytic activities under solid-liquid than under liquid-liquid phase-transfer conditions. The light fluorous macrocycles gave similar, if not better, catalytic activity compared to the parent, non-fluorinated phase-transfer catalyst 2 under solid-liquid conditions in conventional organic solvents in both an aliphatic and an aromatic nucleophilic substitution. N,N′-Bis(1H,1H,2H,2H,3H,3H-perfluoroundecyl)- 4,13-diaza-18-crown-6 (3) was recycled six times in the iodide displacement reaction of 1-bromooctane and four times in the fluoride displacement reaction of 2,4-dinitrochlorobenzene using fluorous solid-phase extraction without any loss in activity.
1-Aryl-3,3-dialkyltriazenes: A convenient synthesis from dry arenediazonium o-benzenedisulfonimides - A high yield break down to the starting dry salts and efficient conversions to aryl iodides, bromides and chlorides
Barbero,Degani,Diulgheroff,Dughera,Fochi
, p. 2180 - 2190 (2007/10/03)
This research comprises three parts. The first part regards the synthesis of 1-aryl-3,3-dialkyltriazenes 3 by reaction of dry arenediazonium o-benzenedisulfonimides 1, also coming from weakly basic aromatic amines with dimethylamine or diethylamine in aqueous solution at 0-5 °C. Yields were usually greater than 90% and there was the possibility of recovering the o-benzenedisulfonimide (5), which could be reused to prepare the salts 1. In the second part it was demonstrated that there is the possibility of reconverting the triazenes 3 into the starting stable dry salts 1 by using 5 as acid. The reactions were carried out in glacial acetic acid at 50-55 °C and normally afforded salts 1 in yields of around 90-99%. The third part concerns the setting up of two procedures for the conversion of 3 to aryl iodides 9, bromides 10 and chlorides 11. Procedure A used the corresponding aqueous hydrogen halides in acetonitrile at r.t. or 60 °C, sometimes in the presence of aqueous HBF4, sometimes Cu powder (25 examples, yields 65%-88%). Procedure B usually used anhydrous methanesulfonic acid and tetraalkylammonium halides in anhydrous acetonitrile at temperatures varying from r.t. to 80 °C, sometimes in the presence of Cu (16 examples, yields 65-88%).
