106-38-7Relevant articles and documents
Novel site-specific one-step bromination of substituted benzenes
Srivastava, Sanjay K.,Chauhan, Prem Man Singh,Bhaduri, Amiya P.
, p. 2679 - 2680 (1996)
Regiospecific bromination of benzene derivatives has been carried out with Me2SO-HBr; this method gives excellent yields of 2-bromobenzaldehyde and 2-bromonitrobenzene; strong ortho- and para-directing monosubstituted benzenes give para-bromo derivatives; a general discussion of the mechanism of these reactions is given.
Selective Halogenation of Aromatic Hydrocarbons with Alumina-Supported Copper(II) Halides
Kodomari, Mitsuo,Satoh, Hiroaki,Yoshitomi, Suehiko
, p. 2093 - 2094 (1988)
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Yaroslavsky
, p. 3395 (1974)
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de la Mare,Harvey
, p. 36,38 (1956)
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Deoxygenation of carbonyl compounds using an alcohol as an efficient reducing agent catalyzed by oxo-rhenium complexes
Bernardo, Joana R.,Fernandes, Ana C.
, p. 2675 - 2681 (2016)
This work describes the first methodology for the deoxygenation of carbonyl compounds using an alcohol as a green solvent/reducing agent catalyzed by oxo-rhenium complexes. The system 3-pentanol/ReOCl3(SMe2)(OPPh3) was successfully employed in the deoxygenation of several aryl ketones to the corresponding alkenes and also in the deoxygenation of aryl aldehydes to alkanes with moderate to excellent yields. The catalyst ReOCl3(SMe2)(OPPh3) can also be used in several catalytic cycles with good activity.
A new method of bromination of aromatic rings by an iso-amyl nitrite/HBr system
Gavara, Laurent,Boisse, Thomas,Rigo, Beno?t,Hénichart, Jean-Pierre
, p. 4999 - 5004 (2008)
A mixture of iso-amyl nitrite/HBr is shown to be a mild and efficient reagent for electrophilic aromatic bromination. The reaction succeeds with slightly activated arenes and heterocyclic compounds. By using HCl instead of HBr, chlorination can also be performed in few cases. The i-amONO2/HBr mixture can also be utilized for bromination in the α-position of electron withdrawing groups. A possible mechanism is briefly discussed.
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Henne,Zimmer
, p. 1362 (1951)
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Bipyridinium and Phenanthrolinium Dications for Metal-Free Hydrodefluorination: Distinctive Carbon-Based Reactivity
Burton, Katherine I.,Elser, Iris,Waked, Alexander E.,Wagener, Tobias,Andrews, Ryan J.,Glorius, Frank,Stephan, Douglas W.
, p. 11730 - 11737 (2021)
The development of novel Lewis acids derived from bipyridinium and phenanthrolinium dications is reported. Calculations of Hydride Ion Affinity (HIA) values indicate high carbon-based Lewis acidity at the ortho and para positions. This arises in part from extensive LUMO delocalization across the aromatic backbones. Species [C10H6R2N2CH2CH2]2+ (R=H [1 a]2+, Me [1 f]2+, tBu [1 g]2+), and [C12H4R4N2CH2CH2]2+ (R=H [2 a]2+, Me [2 b]2+) were prepared and evaluated for use in the initiation of hydrodefluorination (HDF) catalysis. Compound [2 a]2+ proved highly effective towards generating catalytically active silylium cations via Lewis acid-mediated hydride abstraction from silane. This enabled the HDF of a range of aryl- and alkyl- substituted sp3(C?F) bonds under mild conditions. The protocol was also adapted to effect the deuterodefluorination of cis-2,4,6-(CF3)3C6H9. The dications are shown to act as hydride acceptors with the isolation of neutral species C16H14N2 (3 a) and C16H10Me4N2 (3 b) and monocationic species [C14H13N2]+ ([4 a]+) and [C18H21N2]+ ([4 b]+). Experimental and computational data provide further support that the dications are initiators in the generation of silylium cations.
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Brown,Stock
, p. 1421,1422 (1957)
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Halogenation Using N-Halogenocompounds. II. Acid Catalyzed Bromination of Aromatic Compounds with 1,3-Dibromo-5,5-dimethylhydantoin
Eguchi, Hisao,Kawaguchi, Hideichiro,Yoshinaga, Sachiyo,Nishida, Akiko,Nishiguchi, Takeshi,Fujisaki, Shizuo
, p. 1918 - 1921 (1994)
Ring bromination of aromatic compounds using 1,3-dibromo-5,5-dimethylhydantoin in dichloromethane is promoted by the addition of strong acids.Both organic and inorganic acids whose pKa values are lower than -2 showed the promoting effect.This acid-catalyzed bromination is both practical and effective, even for aromatics having electron-withdrawing substituents.
Convenient Synthesis of Aryl Halides from Arylamines via Treatment of 1-Aryl-3,3-dialkyltriazenes with Trimethylsilyl Halides
Ku, Hao,Barrio, Jorge R.
, p. 5239 - 5241 (1981)
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Room-temperature catalytic hydrodefluorination of C(sp3)-F bonds
Scott, Valerie J.,Celenligil-Cetin, Remle,Ozerov, Oleg V.
, p. 2852 - 2853 (2005)
Room-temperature catalytic hydrodefluorination of the strong C(sp3)-F bonds in benzotrifluorides and fluoropentane is catalyzed by Et3Si[B(C6F5)4] and uses Et3SiH as the source of H. Ar-CF
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Bunce
, p. 664,668 (1972)
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OOxidative bromination of activated aromatic compounds using aqueous nitric acid as an oxidant
Joshi, Ashutosh V.,Baidossi, Mubeen,Mukhopadhyay, Sudip,Sasson, Yoel
, p. 568 - 570 (2004)
Oxidative bromination of activated aromatic compounds using alkali metal bromide salts and aqueous nitric acid to the corresponding bromo-derivatives is achieved in a liquid-liquid, two-phase system under ambient conditions. Nitric acid offers a dual function of an oxidant as well as a proton donor, which is essential for oxidative bromination using metal bromide salts. Bromination as well as chlorination could be accomplished with this simple system.
Mixed Micelles of Surface Active Ionic Liquid (SAIL)–Octylphenol Ethoxylate: A Novel Reaction Medium for Selective Oxidation of Toluene to Benzaldehyde
Deore, Tushar S.,Sadgar, Amid L.,Jayaram, Radha V.
, p. 185 - 190 (2020/07/30)
Ionic liquids have been found to be suitable alternatives to volatile organic solvents in chemical transformation. Through a proper choice of cations and anions, the properties of an ionic liquid can be tuned so that it resembles an amphiphile. Such specially designed molecules are known as surface-active ionic liquids (SAIL). Like conventional surfactants, SAIL also form aggregates in an aqueous medium. Studies show that the mixing of SAIL with conventional surfactants leads to synergistic micellization. However, very few reports are available on the application of such systems as reaction media. Present study focuses on the application of mixed micelles of 1-tetradecyl-3-methylimidazol-1-ium bromide, ([C14mim]Br) with nonionic surfactant, Octylphenol ethoxylate with 10 moles of ethylene oxide (OPE-10). Enhanced solubilization and selective catalytic oxidation of toluene using hydrogen peroxide as an oxidant and tungstic acid as a catalyst have been studied in detail using this system.
Poly-N-bromosulfonamide-melamine as a novel brominating reagent for regioselective ipso-bromination of arylboronic acids
Alavinia, Sedigheh,Ghorbani-Vaghei, Ramin
, p. 1269 - 1276 (2021/08/27)
A practical synthetic method for the synthesis of aryl bromide was developed through regioselective bromination of boronic acid in the presence of poly-N-bromosulfonamide-melamine (PBBSM). In this regard, a novel heterogeneous support, cross-linked poly sulfonamide-melamine, has been successfully synthesized to stabilize bromine with high surface functional group density (6.6?mmol Br+/g). The prepared reagent is a novel brominating reagent that combines the effective functions of N-bromosulfonamide, N-bromosulfonamide-melamine, and melamine groups. The structure of PBBSM was characterized using XRD, FT–IR, 1H NMR, TGA, FE-SEM, EDX, and TGA analysis. Graphic abstract: [Figure not available: see fulltext.]
The graphite-catalyzed: ipso -functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes
Badgoti, Ranveer Singh,Dandia, Anshu,Parewa, Vijay,Rathore, Kuldeep S.,Saini, Pratibha,Sharma, Ruchi
, p. 18040 - 18049 (2021/05/29)
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.