13194-68-8Relevant academic research and scientific papers
Microwave-accelerated iodination of some aromatic amines, using urea-hydrogen peroxide addition compound (UHP) as the oxidant
Sosnowski, Maciej,Skulski, Lech
, p. 867 - 870 (2002)
A fast and simple method for the oxidative iodination of some aromatic amines, under microwave irradiation, is reported, using diiodine and the the strongly H-bonded urea-hydrogen peroxide addition compound (H 2NCONH)2...H2O2, UHP) as the oxidant. The reactions were carried out in boiling CHCl3 under a reflux condenser to afford, within 10 minutes, the purified monoiodinated products in 40-80% yields.
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 (2004)
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.
Iodination of activated aromatic compounds using nanostructure solid acid catalyst
Hosseini, Abolfazl,Khalilzadeh, Mohammad A.,Keipour, Hoda,Tajbakhsh, Mahmood
, p. 2407 - 2414 (2012)
Nanoporous silica anchored with sulfonic acid groups effectively catalyzes the iodination of aromatic compounds. The reaction was performed in water using hydrogen peroxide as oxidant. The recyclability of catalyst in green media significantly contributes to the environmental friendliness of the procedure.
NCBSI/KI: A Reagent System for Iodination of Aromatics through in Situ Generation of I-Cl
Palav, Amey,Misal, Balu,Chaturbhuj, Ganesh
, p. 12467 - 12474 (2021/08/24)
In situ iodine monochloride (I-Cl) generation followed by iodination of aromatics using NCBSI/KI system has been developed. The NCBSI reagent requires no activation due to longer bond length, lower bond dissociation energy, and higher absolute charge density on nitrogen. The system is adequate for mono- and diiodination of a wide range of moderate to highly activated arenes with good yield and purity. Moreover, the precursor N-(benzenesulfonyl)benzenesulfonamide can be recovered and transformed to NCBSI, making the protocol eco-friendly and cost-effective.
Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes
Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh
supporting information, (2021/05/26)
Owing to both Lewis and Bronsted acid active sites on sulfated polyborate under homogenous conditions, we were keen on developing iodination protocol of arenes that can meet the requirement of regioselectivity and higher yield. The sulfated polyborate activates N-iodosuccinimide for mono iodination of highly activated substrates viz. phenols, anilines under anhydrous condition. Water tunes sulfated polyborate to generate more Bronsted acid sites resulting in rapid activation of NIS for diiodination. The protocol was equally applicable to diiodination of 4-hydroxyphenylacetic acid to synthesize 4-hydroxy-3,5-diiodophenylacetic acid, an intermediate of tiratricol, a thyroid treatment drug. This protocol was further integrated via one-pot sequential iodination and Sonogashira coupling to synthesize aryl acetylenes, building blocks for the synthesis of a variety of specialty chemicals, API, and natural products.
Preparation method of 2-bromo-5-iodo-benzyl alcohol
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Paragraph 0038-0040, (2021/08/11)
The invention relates to the technical field of organic synthesis, and discloses a preparation method of 2-bromine-5-iodine-benzyl alcohol, which comprises the following steps: S1, o-benzylamine, a phase transfer catalyst, ammonium bicarbonate and an iodination reagent are subjected to iodination reaction to generate 2-methyl-4-iodoaniline; S2, the 2-methyl-4-iodoaniline is subjected to a diazotization reaction and a bromination reaction, and 2-bromine-4-iodobenzene is generated; S3, the 2-bromine-4-iodobenzene reacts with an initiator and N-bromosuccinimide, so as to generate 2-bromine-4-iodobromomethyl benzene; and S4, the 2-bromine-4-iodine bromomethyl benzene reacts with alkali, so as to generate the 2-bromine-5-iodine-benzyl alcohol. The preparation method disclosed by the invention is simple in process operation, few in three wastes and beneficial to industrial production; and no isomer is generated in the iodinated product, reduction of lithium aluminum hydride is not needed, and the problem of high operation risk caused by a large amount of hydrogen generated during reduction of lithium aluminum hydride can be effectively avoided.
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.
Indole and quinoline derivatives and its preparation method and application
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Paragraph 0068; 0069, (2017/02/28)
The invention provides an indoloquinoline derivative, a preparation method and application thereof in preparing antitumor drugs and antiviral drugs. The chemical structure of the indoloquinoline derivative is shown as a formula I. Experiments show that a partly-boric-acid-modified indoloquinoline derivative and a non-boric-acid-modified indoloquinoline derivative have strong inhibition effect on various tumor cell strains, thereby being capable of being used for preparation of the antitumor drugs, and have strong antiviral activity, thereby being capable of being used for preparation of the antiviral drugs.
Photo-induced Metal-Catalyst-Free Aromatic Finkelstein Reaction
Li, Lu,Liu, Wenbo,Zeng, Huiying,Mu, Xiaoyue,Cosa, Gonzalo,Mi, Zetian,Li, Chao-Jun
supporting information, p. 8328 - 8331 (2015/07/15)
The facile iodination of aromatic compounds under mild conditions is a great challenge for both organic and medicinal chemistry. Particularly, the synthesis of functionalized aryl iodides by light has long been considered impossible due to their photo-lability, which actually makes aryl iodides popular starting materials in many photo-substitution reactions. Herein, a photo-induced halogen exchange in aryl or vinyl halides has been discovered for the first time. A broad scope of aryl iodides can be prepared in high yields at room temperature under exceptionally mild conditions without any metal or photo-redox catalysts. The presence of a catalytic amount of elemental iodine could promote the reaction significantly.
