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Acidic ionic liquid supported on silica-coated magnetite nanoparticles as a green catalyst for one-pot diazotization-halogenation of the aromatic amines
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.
Isaad, Jalal
p. 49333 - 49341
(2014)
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The graphite-catalyzed: ipso -functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes
An efficient, metal-free, and sustainable strategy has been described for the ipso-functionalization of phenylboronic acids using air as an oxidant in an aqueous medium. A range of carbon materials has been tested as carbocatalysts. To our surprise, graphite was found to be the best catalyst in terms of the turnover frequency. A broad range of valuable substituted aromatic compounds, i.e., phenols, anilines, nitroarenes, and haloarenes, has been prepared via the functionalization of the C-B bond into C-N, C-O, and many other C-X bonds. The vital role of the aromatic π-conjugation system of graphite in this protocol has been established and was observed via numerous analytic techniques. The heterogeneous nature of graphite facilitates the high recyclability of the carbocatalyst. This effective and easy system provides a multipurpose approach for the production of valuable substituted aromatic compounds without using any metals, ligands, bases, or harsh oxidants.
Badgoti, Ranveer Singh,Dandia, Anshu,Parewa, Vijay,Rathore, Kuldeep S.,Saini, Pratibha,Sharma, Ruchi
p. 18040 - 18049
(2021/05/29)

Hydrogen-Bond-Donor Solvents Enable Catalyst-Free (Radio)-Halogenation and Deuteration of Organoborons
A hydrogen bond donor solvent assisted (radio)halogenation and deuteration of organoborons has been developed. The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Most importantly, compared to literature methods, our conditions are more consistent with the principals of green chemistry (e.g., metal-free, strong oxidant-free, more straightforward conditions).
Yang, Yi,Gao, Xinyan,Zeng, Xiaojun,Han, Junbin,Xu, Bo
supporting information
p. 1297 - 1300
(2020/12/23)

Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange
We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C?P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.
Boehm, Philip,Cacherat, Bastien,Lee, Yong Ho,Martini, Tristano,Morandi, Bill
supporting information
p. 17211 - 17217
(2021/07/02)

Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations
While halogenation is of key importance in synthesis and radioimaging, the currently available repertoire is largely designed to introduce a single halogen per molecule. This report makes the selective introduction of several different halogens accessible. Showcased here is the privileged stability of nontoxic aryl germanes under harsh fluorination conditions (that allow selective fluorination in their presence), while displaying superior reactivity and functional-group tolerance in electrophilic iodinations and brominations, outcompeting silanes or boronic esters under rapid and additive-free conditions. Mechanistic experiments and computational studies suggest a concerted electrophilic aromatic substitution as the underlying mechanism.
Deckers, Kristina,Fricke, Christoph,Schoenebeck, Franziska
supporting information
p. 18717 - 18722
(2020/08/25)

Arene diazonium saccharin intermediates: A greener and cost-effective alternative method for the preparation of aryl iodide
In the current protocol, the arene diazonium saccharin derivatives were initially produced from various substituted aromatic amines; subsequently, these intermediates were treated with a greener organic iodide for the preparation of the aryl iodide. We tried to choose low-cost, commercially available, biodegradable, recoverable, ecofriendly, and safe reagents and solvents. The arene diazonium saccharin intermediates could be stored in the liquid phase into a refrigerator for a long time with no significant loss activity. The outstanding merits of the current protocol (a) included the partial recovering of saccharin and tetraethylammonium salt, (b) reduce the use of solvents and the reaction steps due to eliminating separation and purification of intermediates, (c) good yield of the sterically hindered substrates, and (d) avoid the generation of heavy metal or corrosive waste.
Ghaffari Khaligh, Nader,Rafie Johan, Mohd,Shahnavaz, Zohreh,Zaharani, Lia
p. 535 - 542
(2020/06/01)

ipso-Bromination/iodination of arylboronic acids: Poly(4-vinylpyridine)-Br2/I2 complexes as safe and efficient reagents
Poly(4-vinyl pyridine) supported bromine/iodine complexes were prepared and probed for ipso-bromination/iodination of arylboronic acids. These solid complexes with catalytic amount of additive are found to be safe and efficient reagent system for the ipso-bromination/iodination. The reaction occurs under mild conditions and tolerates various functional groups resulting in products with high selectivity and yields.
Fu, Fang,Gurung, Laxman,Czaun, Miklos,Mathew, Thomas,Prakash, G.K. Surya
supporting information

(2019/08/26)

Zinc-Catalysed Hydroboration of Terminal and Internal Alkynes
A regioselective hydroboration of alkynes has been developed by using commercially available zinc triflate as a catalyst, in the presence of catalytic amount of NaBHEt3. The reaction tolerates a wide range of terminal alkynes having several synthetically useful functional groups and proceeds regioselectively to furnish hydroborated products in moderate to excellent yields. This system shows moderate chemoselectivity towards terminal C≡C bond over terminal and internal C=C bond and internal C≡C bond.
Mandal, Souvik,Mandal, Sayantan,Geetharani
supporting information
p. 4553 - 4556
(2019/08/20)

Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes
Radiopharmaceuticals that incorporate radioactive iodine in combination with single-photon emission computed tomography imaging play a key role in nuclear medicine, with applications in drug development and disease diagnosis. Despite this importance, there are relatively few general methods for the incorporation of radioiodine into small molecules. This work reports a rapid air- and moisture-stable ipso-iododeboronation procedure that uses NIS in the non-toxic, green solvent dimethyl carbonate. The fast reaction and mild conditions of the gold-catalysed method led to the development of a highly efficient process for the radiolabelling of arenes, which constitutes the first example of an application of homogenous gold catalysis to selective radiosynthesis. This was exemplified by the efficient synthesis of radiolabelled meta-[125I]iodobenzylguanidine, a radiopharmaceutical that is used for the imaging and therapy of human norepinephrine transporter-expressing tumours.
Webster, Stacey,O'Rourke, Kerry M.,Fletcher, Conor,Pimlott, Sally L.,Sutherland, Andrew,Lee, Ai-Lan
supporting information
p. 937 - 943
(2017/12/26)

A facile and sustainable protocol to the preparation of aryl iodides using stable arenediazonium bis(trifluoromethylsulfonyl)imide salts via the telescopic process
The preparation of aryl iodides in a telescopic reaction using tert-butyl nitrite as a diazotization reagent and a mixture of bis(trifluoromethane) sulfonamide and glacial acetic acid as a mild acidic agent in ethanol followed by iododediazoniation with tetraethylammonium iodide in water was investigated. The current method has other advantages such as minimized waste by avoiding solvent for the purification of products in diazotization step, simple experimental procedure, and good yield of the sterically hindered aryl amines, metal and strong acid-free waste and environmentally benign conditions. The noteworthy features of this study are the preparation of stable arenediazonium bis(trifluoromethylsulfonyl)imide salts that can be used with no significant loss activity after 1?week and bis(trifluoromethane)sulfonamide was recovered in high yields from reactions.
Khaligh, Nader Ghaffari
(2018/06/04)

Electrochemical Synthesis of Aryl Iodides by Anodic Iododesilylation
An electrochemical access to iodinated aromatic compounds starting from trimethylsilyl-substituted arenes is presented. By design of experiments, highly efficient and mild conditions were identified for a wide range of substrates. A functional group stability test and the synthesis of an important 3-iodobenzylguanidine radiotracer illustrate the scope of this process.
M?ckel, Robert,Hille, Jessica,Winterling, Erik,Weidemüller, Stephan,Faber, Tabea Melanie,Hilt, Gerhard
supporting information
p. 442 - 445
(2018/02/21)

Highly efficient Sandmeyer reaction on immobilized CuI/CuII-based catalysts
Highly effective embodiment of Sandmeyer reaction has been revealed for Cu-based catalysts incorporating ionic liquid on Silochrom support. The most active catalyst (TOF = = 4000–8000 h–1) contains comparable amounts of cuprous and cupric chloride anions. The reported method allows one to carry out the reaction for anilines in the one-pot mode.
Tarkhanova, Irina G.,Gantman, Michail G.,Sigeev, Alexander S.,Maslakov, Konstantin I.,Zelikman, Vladimir M.,Beletskaya, Irina P.
p. 261 - 263
(2018/06/01)

A general electrochemical strategy for the Sandmeyer reaction
Herein we report a general electrochemical strategy for the Sandmeyer reaction. Using electricity as the driving force, this protocol employs a simple and inexpensive halogen source, such as NBS, CBrCl3, CH2I2, CCl4, LiCl and NaBr for the halogenation of aryl diazonium salts. In addition, we found that these electrochemical reactions could be performed using anilines as the starting material in a one-pot fashion. Furthermore, the practicality of this process was demonstrated in the multigram scale synthesis of aryl halides using highly inexpensive graphite as the electrode. A series of detailed mechanism studies have been performed, including radical clock and radical scavenger study, cyclic voltammetry analysis and in situ electron paramagnetic resonance (EPR) analysis.
Liu, Qianyi,Sun, Beiqi,Liu, Zheng,Kao, Yi,Dong, Bo-Wei,Jiang, Shang-Da,Li, Feng,Liu, Guoquan,Yang, Yang,Mo, Fanyang
p. 8731 - 8737
(2018/12/10)

Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids
A convenient, efficient and practical visible-light-induced decarboxylative iodination of aromatic carboxylic acids has been developed, and the corresponding aryl iodides were obtained in good yields. The method shows some advantages including the use of readily available aromatic carboxylic acids as the starting materials, simple and mild conditions, high efficiency, wide substrate scope and tolerance of various functional groups.
Jiang, Min,Yang, Haijun,Jin, Yunhe,Ou, Lunyu,Fu, Hua
supporting information
p. 1572 - 1577
(2018/06/26)

Synthesis of plasmodione metabolites and 13C-enriched plasmodione as chemical tools for drug metabolism investigation
Malaria is a tropical parasitic disease threatening populations in tropical and sub-tropical areas. Resistance to antimalarial drugs has spread all over the world in the past 50 years, thus new drugs are urgently needed. Plasmodione (benzylmenadione series) has been identified as a potent antimalarial early lead drug, acting through a redox bioactivation on asexual and young sexual blood stages. To investigate its metabolism, a series of plasmodione-based tools, including a fully 13C-labelled lead drug and putative metabolites, have been designed and synthesized for drug metabolism investigation. Furthermore, with the help of UHPLC-MS/MS, two of the drug metabolites have been identified from urine of drug-treated mice.
Feng, Liwen,Lanfranchi, Don Antoine,Cotos, Leandro,Cesar-Rodo, Elena,Ehrhardt, Katharina,Goetz, Alice-Anne,Zimmermann, Herbert,Fenaille, Fran?ois,Blandin, Stephanie A.,Davioud-Charvet, Elisabeth
p. 2647 - 2665
(2018/04/27)

Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide
A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.
Mukhopadhyay, Sushobhan,Batra, Sanjay
supporting information
p. 14622 - 14626
(2018/09/21)

An efficient gram scale synthesis of aryl iodides from aryl diazofluoroborates in water under mild conditions
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.
Gholap, Somnath S.
p. 594 - 599
(2018/06/26)

A simple and efficient iodination of aromatic compounds using I2/Choline Chloride/K2S2O8
A simple and efficient method for the iodination of aromatic compounds has been achieved in the presence of molecular iodine, choline chloride and potassium peroxodisulfate at 65 °C in acetonitrile. The rate of conversion of aromatic compounds into iodoaromatic compounds was promoted by in situ formed choline peroxodisulfate. This protocol provides an efficient access to iodoarenes with operational simplicity, good functional group tolerance and a moderate to good product yield.
Parthiban,Joel Karunakaran
p. 1659 - 1663
(2018/06/12)

A one-pot radioiodination of aryl amines: Via stable diazonium salts: Preparation of 125I-imaging agents
An operationally simple, one-pot, two-step tandem procedure that allows the incorporation of radioactive iodine into aryl amines via stable diazonium salts is described. The mild conditions are tolerant of various functional groups and substitution patterns, allowing late-stage, rapid access to a wide range of 125I-labelled aryl compounds and SPECT radiotracers.
Sloan, Nikki L.,Luthra, Sajinder K.,McRobbie, Graeme,Pimlott, Sally L.,Sutherland, Andrew
supporting information
p. 11008 - 11011
(2017/10/13)

Late stage iodination of biologically active agents using a one-pot process from aryl amines
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.
Sloan, Nikki L.,Luthra, Sajinder K.,McRobbie, Graeme,Pimlott, Sally L.,Sutherland, Andrew
p. 54881 - 54891
(2017/12/12)

Containing diphenylacetylene cyclopentadienyl iron salt such two-photon absorbing material and its preparation method
The invention relates to three cyclopentadienyl iron salt two-photon absorption materials having a diphenylacetylene group and a preparation method thereof; a diphenylacetylene structure and a cationic cyclopentadienyl iron receptor are jointly composed of a D-(pi)-A type two-photon absorption functional group, and thus the three synthesized novel cyclopentadienyl iron salts have a strong two-photon absorption ability at 532 nm, and has great application value in the two-photon photoetching field when used as the two-photon absorption type cationic photo-initiator.
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Paragraph 0042-0044; 0051; 0052

(2017/08/25)

Salicylic Acid-Catalyzed One-Pot Hydrodeamination of Aromatic Amines by tert-Butyl Nitrite in Tetrahydrofuran
A significant acceleration in the hydrodeamination of in situ formed diazonium salts (from aromatic amines) has been observed in the presence of 10-mol% salicylic acid, using tetrahydrofuran as the hydrogen donor. The reaction proceeds efficiently at 20 °C for a wide range of substituted anilines, even at 10-mmol scale, without any other additive. The same protocol has been adapted to the selective deuterodeamination of some aromatic amines. Control experiments clearly show that aryl radicals are involved in the reaction mechanism. (Figure presented.).
Felipe-Blanco, Diego,Alonso, Francisco,Gonzalez-Gomez, Jose C.
supporting information
p. 2857 - 2863
(2017/08/23)

N-Iodosuccinimide (NIS) in Direct Aromatic Iodination
N-Iodosuccinimide (NIS) in pure trifluoroacetic acid (TFA) offers a time-efficient and general method for the iodination of a wide range of mono- and disubstituted benzenes at room temperature, as demonstrated in this paper. The starting materials were generally converted into mono-iodinated products in less than 16 hours at room temperature, without byproducts. A few deactivated substrates needed addition of sulfuric acid to increase the reaction rate. Another exception was methoxybenzenes that preferentially were iodinated by NIS in acetonitrile with only catalytic amounts of TFA.
Bergstr?m, Maria,Suresh, Ganji,Naidu, Veluru Ramesh,Unelius, C. Rikard
p. 3234 - 3239
(2017/06/21)

Nucleophile promoted gold redox catalysis with diazonium salts: C-Br, C-S and C-P bond formation through catalytic Sandmeyer coupling
Gold-catalyzed C-heteroatom (C-X) coupling reactions are evaluated without using sacrificial oxidants. Vital to the success of this methodology is the nucleophile-assisted activation of aryldiazonium salts, which could be an effective oxidant for converting Au(i) to Au(iii) even without the addition of an assisting ligand or photocatalyst. By accelerating the reaction kinetics to outcompete C-C homo-coupling or diazonium dediazoniation, gold-catalyzed Sandmeyer reactions were achieved with different nucleophiles, forming C-Br, C-S and C-P bonds in high yields and selectivities.
Peng, Haihui,Cai, Rong,Xu, Chang,Chen, Hao,Shi, Xiaodong
p. 6190 - 6196
(2016/09/03)

Easy Access to Difluoromethylene-Containing Arene Analogues through Palladium-Catalysed C–H Olefination
An efficient palladium-catalysed ortho-C–H olefination of α,α-difluorophenylacetic acid derivatives using 8-aminoquinoline as a bidentate directing group has been developed. A range of olefinated arenes can thus be synthesized in a concise way. This reaction provides an easy and straightforward route to a panel of difluoromethylated arene analogues in moderate to good yields, with a satisfactory tolerance of common functional groups. Transformation of the products into a variety of other difluoromethylene-containing compounds demonstrates the utility of this method.
Shao, Changdong,Shi, Guangfa,Zhang, Yanghui
supporting information
p. 5529 - 5538
(2016/11/25)

Practical and efficient ipso-iodination of arylboronic acids via KF/I2 system
A facile and effective iododeboronation of variously substituted aryl and heteroarylboronic acids through activation and subsequent ipso-introduction of iodine is presented. The use of KF and I2 at 80 °C in 1,4-dioxane furnishes iodinated compounds in high yields.
Tramutola, Francesco,Chiummiento, Lucia,Funicello, Maria,Lupattelli, Paolo
p. 1122 - 1123
(2015/02/19)

A practical and general ipso iodination of arylboronic acids using N-iodomorpholinium iodide (NIMI) as a novel iodinating agent: mild and regioselective synthesis of aryliodides
A mild and efficient protocol for the ipso-iodination of aryl boronic acids using N-iodomorpholinium iodide (NIMI) generated in situ from morpholine and molecular iodine as a novel iodinating agent has been developed. The addition of a catalytic amount of copper iodide found to promote rate enhancement of the iodination reaction and dramatic increase in the yield depending upon the nature of the boronic acid was observed. The mechanistic study revealed that depending upon the nature of the substrate, either the classical ipso substitution or copper catalysed iododeborylation pathway overall dominates the present iodination reaction. The features such as mild reaction conditions, operational simplicity, high to excellent yields, excellent functional group compatibility and low catalyst loading make this method potentially useful in organic synthesis.
Tale,Toradmal,Gopula
p. 84910 - 84919
(2015/10/28)

PROCESS FOR THE PREPARATION OF N-IODOAMIDES
The present invention provides new stable crystalline N-iodoamides - 1-iodo- 3,5,5-trimethylhydantoin (1-ITMH) and 3-iodo-4,4-dimethyl-2-oxazolidinone (IDMO). The present invention further provides a process for the preparation of organic iodides using N-iodoamides of this invention and recovery of the amide co-products from waste water.
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Paragraph 00234-00235

(2015/05/26)

COMPOUND FOR ORGANIC ELECTROLUMINESCENT DEVICE AND ORGANIC ELECTROLUMINESCENT DEVICE INCLUDING THE SAME
This invention relates to a compound for an organic electroluminescent device and to an organic electroluminescent device including the same. This compound for an organic electroluminescent device including the same is improved in thermal stability and light emission efficiency. When this compound is used as a hole transport layer material, a triplet energy of a phosphorescent light emitting material is increased, thus improving the efficiency of the organic electroluminescent device.
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(2015/10/28)

Ni(II) catalyzed bromination of aryl C-H bonds
Bromination of unactivated aromatic C-H bonds without directing and/or chelating groups was achieved by employing an air stable N-heterocyclic Ni(II) complex. PhI(OAC)2and N-bromosuccinimide have been used as the oxidizing agent and the bromine source, respectively. Yields for bromination are as high as >99%, especially in presence of electron-withdrawing groups like -NO2and -CF3. This is a rare report on C-H bond activation with Ni(II) where, instead of homo C-C coupling, reductive elimination to form C-halogen could be achieved.
Bhattacharya, Moumita,Cluff, David B.,Das, Siddhartha
p. 238 - 241
(2015/02/20)

Metal-free one-pot synthesis of benzofurans
Ethyl acetohydroxamate was efficiently arylated with diaryliodonium salts at room temperature under transition-metal-free conditions. The obtained O-arylated products were reacted in situ with ketones under acidic conditions to yield substituted benzo[b]furans through oxime formation, [3,3]-rearrangement, and cyclization in a fast and operationally simple one-pot fashion without using excess reagents. Alternatively, the O-arylated products could be isolated or transformed in situ to aryloxyamines or O-arylaldoximes. The methodology was applied to the synthesis of Stemofuran A and the formal syntheses of Coumestan, Eupomatenoid 6, and (+)-machaeriol B. Just add salt! A metal-free, room temperature arylation of ethyl acetohydroxamate, followed by an in situ reaction with ketones under acidic conditions yielded substituted benzo[b]furans in a fast and operationally simple one-pot fashion without using excess reagents (see scheme). Alternatively, the O-arylated products could be isolated, hydrolyzed in situ to aryloxyamines, or transformed to O-arylaldoximes. The efficiency of the methodology was demonstrated by the formal synthesis of several biologically active benzofurans.
Ghosh, Raju,Stridfeldt, Elin,Olofsson, Berit
supporting information
p. 8888 - 8892
(2014/07/22)

Tetraarylcyclobutadienecyclopentadienylcobalt complexes: Synthesis, electronic spectra, magnetic circular dichroism, linear dichroism, and TD DFT calculations
The known (tetraphenyl-η4-cyclobutadiene)- η5-cyclopentadienylcobalt (1) and a series of its new substituted derivatives have been prepared. The electronic states of a few representatives have been characterized by absorption and magnetic circular dichroism. Time-dependent density functional theory has been used to arrive at spectral assignments for several prominent low-energy bands. The absorption spectra of the radical ions of 1 have also been recorded.
Kottas, Gregg S.,Brotin, Thierry,Schwab, Peter F. H.,Gala, Kamal,Havlas, Zdenek,Kirby, James P.,Miller, John R.,Michl, Josef
p. 3251 - 3264
(2014/08/05)

Aryl diazonium nanomagnetic sulfate and potassium iodide: An iodination process
A simple and efficient procedure for the synthesis of iodoarenes is developed which involves the sequential diazotization-iodination of aromatic amines with sodium nitrite, nanomagnetic supported sulfonic acid, and potassium iodide under solvent-free conditions at room temperature.
Kolvari, Eskandar,Amoozadeh, Ali,Koukabi, Nadiya,Otokesh, Somayeh,Isari, Mohsen
supporting information
p. 3648 - 3651
(2014/06/23)

Tribromoisocyanuric acid in trifluoroacetic acid: An efficient system for smooth brominating of moderately deactivated arenes
Moderately deactivated arenes are efficiently brominated by the reaction with tribromoisocyanuric acid (0.34 mol equiv) in trifluoroacetic acid at room temperature in 48-85% isolated yield. This medium avoids the polybromination of the substrate, observed in the same reaction performed in 98% H 2SO4. Georg Thieme Verlag Stuttgart · New York.
De Almeida, Leonardo S.,De Mattos, Marcioc. S.,Esteves, Pierre M.
p. 603 - 606
(2013/04/10)

Halogenation and DNA cleavage via thermally stable arenediazonium camphorsulfonate salts
A series of stable arenediazonium camphorsulfonate salts (2a-2j) were synthesized by simple diazotization of several aromatic amines in the presence of sodium nitrite and camphorsulfonic acid. All the new arenediazonium camphorsulfonates, which were characterized by multinuclear (1H and 13C) NMR, IR, DSC, and X-ray diffraction analysis (2e and 2f) provide unambiguous proof for the molecular structures of 2e and 2f. The efficient application of these salts in halogenation reactions was studied in solvent and solvent-free conditions and the DNA cleavage activity was also assessed. These arenediazonium camphorsulfonate salts are noticed as efficient DNA cleaving agents.
Vajpayee, Vaishali,Moon, Mi Eun,Lee, Sunmi,Ravikumar, Sambandam,Kim, Hyunuk,Ahn, Byungchan,Choi, Seoyoon,Hong, Soon Ho,Chi, Ki-Whan
p. 3511 - 3517
(2013/04/23)

Nitrite ionic liquid as a new reagent for in situ synthesis of aryl iodides and azides
A new ionic liquid, 1-methyl-3-(2-[2-(1-methyl-1H-imidazol-3-ium-3-yl)ethyloxy] ethyl)-1H-imidazol-3-ium dinitrite, was synthesized. This ionic liquid was used as a convenient nitrosonium source in diazotization of aryl amines into their corresponding diazonium salts, which were converted into aryl iodides and aryl azides using potassium iodide or sodium azide, respectively. Various aryl amines possessing electron-withdrawing groups or electron-donating groups were converted into the corresponding aryl iodides and aryl azides in excellent yields. Advantages of this methodology are the use of mild reaction conditions, short reaction times, and avoiding the use of toxic solvents.
Eshghi, Hossein,Bakavoli, Mehdi,Ghasemzadeh, Marjan
p. 3999 - 4007
(2015/06/08)

Iron-catalyzed cross-coupling reaction: Recyclable heterogeneous iron catalyst for selective olefination of aryl iodides in poly(ethylene glycol) medium
An environmentally friendly iron-based catalyst supported on acac-functionalized silica was successfully prepared and evaluated as a heterogeneous catalyst for Mizoroki-Heck reaction of aryl iodides and olefins. Our catalytic system showed good activities that were comparable to that of palladium catalysts. The catalyst was simply recovered from the reaction mixture and recycled five times. Furthermore, the reaction was carried out in poly(ethylene glycol) as a green solvent. Interestingly, using this catalyst, aryl iodides were selectively olefinated in the presence of aryl bromides.
Hajipour, Abdol Reza,Azizi, Ghobad
supporting information
p. 1030 - 1034
(2013/07/26)

Bromination of aromatic compounds using an Fe2O 3/zeolite catalyst
The catalytic bromination of non-activated aromatic compounds has been achieved using an Fe2O3/zeolite catalyst system. FeBr 3 was identified as the catalytic species, formed in situ from HBr and Fe2O3. The catalyst was easy-to-handle and cost effective and could also be recycled. The reaction system was also amenable to the one-pot sequential bromination/C-C bond formation of benzene.
Nishina, Yuta,Takami, Keishi
supporting information
p. 2380 - 2383
(2013/02/21)

Tetraflic acid (1,1,2,2-Tetrafluoroethanesulfonic acid, HC 2F4SO3H) and gallium tetraflate as effective catalysts in organic synthesis
Tetraflic acid offers ample acidity for various organic reactions that require high acidity. Its gallium(III) salt is an efficient catalyst under mild condtions for synthetic transformations such as the ketonic Strecker reaction for the synthesis of fluorinated α-amino nitriles and condensation- cyclzation reactions using suitable fluoro ketones and 1,2-disubstituted benzenes for the direct preparation of 5-membered or 6-membered fluorinated heterocycles. Copyright
Prakash, G. K. Surya,Mathew, Thomas,Panja, Chiradeep,Kulkarni, Aditya,Olah, George A.,Harmer, Mark A.
p. 2163 - 2171
(2012/11/07)

Halodeboronation of organotrifluoroborates using tetrabutylammonium tribromide or cesium triiodide
Halodeboronation of organotrifluoroborates using commercially available tetrabutylammonium tribromide (TBATB) or cesium triiodide in aqueous medium is reported. The mild, transition metal-free method has proven to be tolerant of a wide range of functional groups. High regio- and chemoselectivity are observed. Two synthetic routes to (Z)-dibromoalkenes from alkynes, through stereodefined (Z)-2-bromoalkenyltrifluoroborates and (Z)-1,2-bis(boryl) alkenyltrifluoroborates, have been developed using the TBATB mediated bromodeboronation as the key step.
Yao, Min-Liang,Kabalka, George W.,Blevins, David W.,Reddy, Marepally Srinivasa,Yong, Li
experimental part
p. 3738 - 3743
(2012/06/30)

Hydroxy- and aminophenyl radicals from arenediazonium salts
Arenediazonium salts are well-known sources of aryl radicals; however, the hydroxy- and amino-substituted derivatives 1, 2, and 3, which lead to the respective formation of radicals 4, 5, and 6, have rarely been employed in synthetic organic chemistry so far. New synthetic applications of these species have been found, and the properties that may have previously hindered their successful use have been investigated. Copyright
Pratsch, Gerald,Anger, Christian A.,Ritter, Katharina,Heinrich, Markus R.
scheme or table
p. 4104 - 4108
(2011/05/12)

PROCESS FOR THE PREPARATION OF IODIDES
This invention is directed to a process for the preparation of high yield alkyl or aryl iodide from its corresponding carboxylic acid using N-iodo amides.
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Page/Page column 34

(2012/01/05)

Synthesis of triphenylamine-modified arylates and ketones via suzuki coupling reactions
A series of triphenylamine-mdified arylates and ketones were synthesized via Pd-catalyzed Suzuki coupling reaction of triphenylamine boronic acid with aryl bromide. The triphenylamine boronic acid was synthesized by iodization of 4-bromoaniline, Ullmann reaction of 1-bromo-4-iodobenzene with diphenylamine, and boronic acidification of 4-bromotriphenylamine.
Wang, Jian,Yang, Chang-Jian,Peng, Hua-Nan,Deng, Yang-Sheng,Gao, Xi-Cun
experimental part
p. 832 - 840
(2011/04/22)

Application of [Hcpy]HSO4 Broensted acidic ionic liquid for the synthesis of aryl iodides from aromatic amines
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Hajipour, Abdol Reza,Seddighi, Mohadeseh
experimental part
p. 292 - 296
(2011/07/31)

Superelectrophilic iodination of deactivated arenes with triiodoisocyanuric acid
The reaction of triiodoisocyanuric acid (TICA) with deactivated arenes in acidic medium led to the efficient and regioselective formation of the corresponding iodoarenes, in 55-88% isolated yield. The acidity of the medium was found to be the most important factor influencing the electrophilic iodination of weakly nucleophilic substrates by TICA. Georg Thieme Verlag Stuttgart New York.
Da Ribeiro, Rodrigo S.,Esteves, Pierre M.,De Mattos, Marcio C. S.
experimental part
p. 739 - 744
(2011/04/24)

Efficient iodination of aromatic compounds using potassium ferrate supported on montmorillonite
Potassium ferrate impregnated on montmorillonite is a mild, cheap, and non-toxic reagent for the iodination of phenols, including naphthol, aromatic amines, and heterocyclic substrates in fair to excellent yields by a simple isolation procedure.
Keipour, Hoda,Khalilzadeh, Mohammad A.,Mohtat, Bita,Hosseini, Abolfazl,Zareyee, Daryoush
experimental part
p. 1427 - 1430
(2012/06/01)

NO-CARRIER-ADDED NUCLEOPHILIC [F-18] FLUORINATION OF AROMATIC COMPOUNDS
Phenyliodonium ylide derivatives substituted with electron donating as well as electron withdrawing groups on the aromatic ring are shown for use as precursors in aromatic nucleophilic substitution reactions. The iodonium ylide group is substituted by nucleophiles such as halide ions to provide the corresponding haloaryl derivatives. No- carrier-added [F-18]fluoride ion exclusively substitutes the iodonium ylide moiety in these derivatives and provides high specific activity F- 18 labeled fluoro derivatives. Protected L-dopa-6-iodonium ylide derivative have been synthesized as a precursors for the preparation of no-carrier-added 6-[F- 18]fluoro-L-dopa. The iodonium ylide group in this L-dopa.derivative is nucleophilically substituted by no-carrier-added [F-18]fluoride ion to provide a [F-18]fluoro intermediates which upon acid hydrolysis yielded 6-[F- 18]fluoro-L-dopa.
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Page/Page column 11-12

(2010/11/03)

Efficient and economic halogenation of aryl amines via arenediazonium tosylate salts
Arenediazonium tosylate salts have been successfully employed as a new and efficient reagent in halogenation reactions. A novel and economic protocol has been developed for the bromination and chlorination of various anilines using arenediazonium tosylate salts. A wide variety of reaction conditions were studied in acetonitrile at either room temperature or 60 °C in the presence or absence of catalyst with good to excellent yields. A surprising result showed the formation of acetanilides as a major product of aniline and methyl-substituted aniline halogenations in high yields.
Lee, Young Min,Moon, Mi Eun,Vajpayee, Vaishali,Filimonov, Victor D.,Chi, Ki-Whan
experimental part
p. 7418 - 7422
(2010/10/01)

An expeditious and environmentally benign preparation of aryl halides from aryl amines by solvent-free grinding
An efficient solvent-free methodology for conversion of various aryl amines into bromides and chlorides via arenediazonium tosylate salts under grinding conditions is disclosed. This new methodology not only avoids the use of strong acids and expensive reagents for diazotization-halogenation reactions, but also decreases the amount of organic waste from the reaction process.
Moon, Mi Eun,Choi, Younghwa,Lee, Young Min,Vajpayee, Vaishali,Trusova, Marina,Filimonov, Victor D.,Chi, Ki-Whan
scheme or table
p. 6769 - 6771
(2011/03/17)

METHOD OF PRODUCING IODIZING AGENT, AND METHOD OF PRODUCING AROMATIC IODINE COMPOUND
A method of the present invention, for producing an iodizing agent, includes the step of electrolyzing iodine molecules in a solution by using an acid as a supporting electrolyte. This realizes (i) a method of producing an iodine cation suitable for use as an iodizing agent that does not require a sophisticated separation operation after iodizing reaction is completed, and (ii) an electrolyte used in the method. Further, a method of the present invention, for producing an aromatic iodine compound, includes the step of causing an iodizing agent, and an aromatic compound whose nucleus has one or more substituent groups and two or more hydrogen atoms, to react with each other under the presence of a certain ether compound. This realizes such a method of producing an aromatic iodine compound that position selectivity in iodizing reaction of an aromatic compound is improved.
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Page/Page column 11

(2010/05/13)