4949-69-3Relevant academic research and scientific papers
A novel DMSO-assisted regioselective iodination of aniline analogues
Bovonsombat, Pakorn,Lorpaiboon, Wanutcha,Laoboonchai, Sarocha,Sriprachaya-anunt, Prima,Yimkosol, Warangkana,Siriphatcharachaikul, Natthapatch,Siricharoensang, Pornpawit,Kangwannarakul, Terawee,Maeda, Jin,Losuwanakul, Satreerat,Mahesh Abhyankar, Maitraye
, (2020/10/05)
A metal- and oxidant-free electrophilic iodination of aniline analogues was achieved in high to excellent yields at room temperature in MTBE with 0 or 3.5 equivalents of DMSO. Examined substituents include N-alkyl, N,N-dialkyl, N-morpholinyl and N-piperazinyl as well as methyl, Br, CN and CO2CH3 aryl ring substitutions.
Sodium sulfate-hydrogen peroxide-sodium chloride adduct: selective protocol for the oxidative bromination, iodination and temperature dependent oxidation of sulfides to sulfoxides and sulfones
Gayakwad, Eknath M.,Patel, Khushbu P.,Shankarling, Ganapati S.
supporting information, p. 6001 - 6009 (2019/04/17)
The regioselective bromination and iodination of unprotected aromatic primary amines using enclathrated hydrogen peroxide as an oxidant under mild conditions has been developed, in which potassium bromide (KBr) and potassium iodide (KI) were used as brominating and iodinating agents, respectively. The adduct shows not only regioselectivity for para- or ortho-isomers but also a remarkable chemoselectivity for monobromination. Selective oxidation of sulfides to sulfoxides and sulfones has also been studied and good to excellent yields of the desired products were obtained. Acetic acid was found to be the solvent of choice for these reactions. This simple method represents an ecologically benign and alternative pathway for the oxidative halogenation of anilines and the oxidation of sulfides to sulfoxides and sulfones.
Regioselective iodination of aryl amines using 1,4-dibenzyl-1,4-diazoniabicyclo [2.2.2] octane dichloroiodate in solution and under solvent-free conditions
Alikarami, Mohammad,Nazarzadeh, Somayeh,Soleiman-Beigi, Mohammad
, p. 157 - 162 (2015/01/30)
1,4-Dibenzyl-1,4-diazoniabicyclo[2.2.2]octane dichloroiodate is an efficient and regioselective reagent for iodination of aryl amines. A wide variety of aryl amines in reaction with this reagent afforded regioselectively iodinated products. The iodination reaction can be carried out in solution or under solvent-free condition at room temperature.
Preparation and characterization of Ni/mZSM-5 zeolite with a hierarchical pore structure by using KIT-6 as silica template: An efficient bi-functional catalyst for the reduction of nitro aromatic compounds
Mazaheri, Omid,Kalbasi, Roozbeh Javad
, p. 34398 - 34414 (2015/04/27)
Ni/mZSM-5 and Ni/H-mZSM-5 were synthesized as hierarchical (micro/meso porous) ZSM-5 zeolites by an indirect template method for the first time. The resulting zeolite materials exhibited significantly enhanced diffusional properties in comparison to purely microporous zeolite materials. The structural and morphological characterization of the prepared catalysts was investigated using XRD, BET, atomic absorption spectroscopy, FT-IR, 27Al-MAS NMR, SEM, TEM, XPS and DRS-UV techniques. These hierarchical zeolites were used as acid-metal bi-functional heterogeneous catalysts for hydride transfer in the reduction of nitro aromatic compounds. In these reactions, NaBH4 was used as a reducing agent. Excellent yields at room temperature and very short reaction times in aqueous media conditions were obtained. Reusability experiments showed the excellent stability of Ni/mZSM-5 and Ni/H-mMZSM-5 and the catalysts could be reused 7 times without much loss of activity in reduction of nitro aromatic compounds. Surprisingly, the acid form of Ni/H-mZSM-5 showed much higher activity than that of Ni/mZSM-5. High yield, short reaction time, green solvent (water), room temperature, no by-product, the easy reusability of catalysts and the low amounts of catalyst required are some of the advantages of these catalysts.
P-Iodinations in hydrocarbon media: Continuous flow reactor application
Slocum,Tekin, Kristen C.,Nguyen, Quang,Whitley, Paul E.,Reinscheld, Thomas K.,Fouzia, Begum
experimental part, p. 7141 - 7145 (2012/01/05)
Regiospecific iodination of aryl amines, that is, aryl compounds possessing strong electron donating groups (EDG's) in the p-position, is described. This procedure features not only the unique use of hydrocarbon media for such substitutions but also the absence of any oxidants aside from iodine itself. Further potential of this hydrocarbon media based electrophilic aromatic substitution is demonstrated by the coupling of the iodination with an in situ halogen/lithium exchange and product forming nucleophilic addition in a batch process. The protocol was ultimately scaled to a continuous flow reactor using an isolated p-iodoarylamine. Constituted as described, these procedures possess enhanced atom-economical, green and safety aspects compared to existing literature protocols.
Microwave-accelerated or conventionally heated iodination reactions of some aromatic amines, using ortho-periodic acid as the oxidant
Sosnowski, Maciej,Skulski, Lech,Wolowik, Katarzyna
, p. 617 - 621 (2007/10/03)
A fast and simple method for the oxidative iodination of some aromatic amines, either under microwave irradiation or conventional heating, is reported, using diiodine and ortho-periodic acid as the oxidant. The reactions were carried out in boiling CH2Cl2 solutions under a reflux condenser. For the microwave assisted reactions, the reaction times were always notably shortened, but the yields were usually less influenced as compared with the conventional method.
Novel ZnX2-modulated Pd/C and Pt/C catalysts for chemoselective hydrogenation and hydrogenolysis of halogen-substituted nitroarenes, alkenes, benzyl ethers, and aromatic ketones
Wu, George,Huang, Mingsheng,Richards, Monique,Poirier, Marc,Wen, Xin,Draper, Richard W.
, p. 1657 - 1660 (2007/10/03)
Novel ZnX2-modulated Pd/C and Pt/C catalysts were developed to chemoselectively hydrogenate halogen-substituted nitroarenes, alkenes, benzyl ethers, and aromatic ketones.
Tetramethylammonium dichloroiodate: An efficient and environmentally friendly iodination reagent for iodination of aromatic compounds under mild and solvent-free conditions
Hajipour, Abdol R.,Arbabian, Marty,Ruoho, Arnold E.
, p. 8622 - 8624 (2007/10/03)
Tetramethylammonium dichloroiodate (1, TMADCI) as a mild and efficient iodination reagent was prepared. Iodination of different aromatic compounds with this reagent takes place fast and with high yields under solvent-free conditions.
Iodination with Potassium Permanganate/Hydroiodic Acid/Acetonitrile Reagent
Chen, Jyh-An,Lin, Ching-Shan,Liu, Lilian Kao
, p. 95 - 99 (2007/10/03)
Iodination of various aromatic amines proceeds smoothly with a preformed homogeneous mixture of hydroiodic acid potassium permanganate in acetonitrile. para-Substituted products were obtained in high yields (71-78%) within twelve hours at room temperature. With a slight modification of the permanganate, hydroiodic acid and substrate ratio, iodination of alkynes to vic-diiodoalkenes can be carried out at 60 °C in 65-87% yield.
Halogenation Using Quaternary Ammonium Polyhalides. VII. Iodination of Aromatic Amines by Use of Benzyltrimethylammonium Dichloroiodate(1-)
Kajigaeshi, Shoji,Kakinami, Takaaki,Yamasaki, Hiromichi,Fujisaki, Shizuo,Okamoto, Tsuyoshi
, p. 600 - 602 (2007/10/02)
The reaction of aromatic amines with benzyltrimethylammonium dichloroiodate(1-) in dichloromethane-methanol in the presence of calcium carbonate powder for several hours at room temperature gave selectively iodo-substituted aromatic amines in good yields.
