- Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange
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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
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supporting information
p. 17211 - 17217
(2021/07/02)
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- Photochemically Activated Dimagnesium(I) Compounds: Reagents for the Reduction and Selective C?H Bond Activation of Inert Arenes
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The photochemical activation of dimagnesium(I) compounds, and subsequent high yielding, regioselective reactions with inert arenes are reported. Irradiating benzene solutions of [{(ArNacnac)Mg}2] (ArNacnac=[HC(MeCNAr)2]?; Ar=2,6-diisopropylphenyl (Dip) or 2,4,6-tricyclohexylphenyl (TCHP)) with blue or UV light, leads to double reduction of benzene and formation of the “Birch-like” cyclohexadienediyl bridged compounds, [{(ArNacnac)Mg}2(μ-C6H6)]. Irradiation of [{(DipNacnac)Mg}2] in toluene, and each of the three isomers of xylene, promoted completely regio- and chemo-selective C?H bond activations, and formation of [(DipNacnac)Mg(Ar′)] (Ar′=meta-tolyl; 2,3-, 3,5- or 2,5-dimethylphenyl), and [{(DipNacnac)Mg(μ-H)}2]. Fluorobenzene was cleanly defluorinated by photoactivated [{(DipNacnac)Mg}2], leading to biphenyl and [{(DipNacnac)Mg(μ-F)}2]. Computational studies suggest all reactions proceed via photochemically generated magnesium(I) radicals, which reduce the arene substrate, before C?H or C?F bond activation processes occur.
- Jones, Dafydd D. L.,Douair, Iskander,Maron, Laurent,Jones, Cameron
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supporting information
p. 7087 - 7092
(2021/03/01)
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- Synthesis of biaryl compounds via Suzuki homocoupling reactions catalyzed by metal organic frameworks encapsulated with palladium nanoparticles
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Heterogeneous homocoupling reactions of phenylboronic acids were greatly accelerated via Suzuki homocoupling reactions. In this work, a tandem route was designed which firstly one part of phenylboronic acids reacted with iodine to form iodobenzenes, then another part of phenylboronic acids coupled with iodobenzenes to produce biaryl compounds. The tandem reaction were catalyzed by a bifunctional heterogeneous catalyst of metal organic frameworks encapsulated with palladium nanoparticles (Pd?MOFs). This strategy for forming symmetric C-C bond between benzene rings has obvious advantages such as high efficiency, easy separation, good recyclability and no addition of toxic halogenated benzene.
- Bao, Yan-Sai,Cui, Xin-Yu,Han, Zheng-Bo,Li, Xin,Tang, Hong,Yang, Ming,Zhang, Yu-Yang,Zhao, Kun,Zhou, Mei-Li
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- Generation of Organozinc Reagents by Nickel Diazadiene Complex Catalyzed Zinc Insertion into Aryl Sulfonates
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The generation of arylzinc reagents (ArZnX) by direct insertion of zinc into the C?X bond of ArX electrophiles has typically been restricted to iodides and bromides. The insertions of zinc dust into the C?O bonds of various aryl sulfonates (tosylates, mesylates, triflates, sulfamates), or into the C?X bonds of other moderate electrophiles (X=Cl, SMe) are catalyzed by a simple NiCl2–1,4-diazadiene catalyst system, in which 1,4-diazadiene (DAD) stands for diacetyl diimines, phenanthroline, bipyridine and related ligands. Catalytic zincation in DMF or NMP solution at room temperature now provides arylzinc sulfonates, which undergo typical catalytic cross-coupling or electrophilic substitution reactions.
- Klein, Philippe,Lechner, Vivien Denise,Schimmel, Tanja,Hintermann, Lukas
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supporting information
p. 176 - 180
(2019/12/11)
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- A general electrochemical strategy for the Sandmeyer reaction
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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
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p. 8731 - 8737
(2018/12/10)
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- Direct Pd(II)-Catalyzed Site-Selective C5-Arylation of 2-Pyridone Using Aryl Iodides
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A straightforward Pd(II)-catalyzed general strategy was developed for the C5-selective arylation of the 2-pyridone core with easily available aryl iodides. The transformation was highly regioselective and accomplished with a wide scope and functional group tolerance. Silver nitrate played a crucial role in this direct site-selective arylation. The method was extended to synthesize biologically active molecules.
- Maity, Saurabh,Das, Debapratim,Sarkar, Souradip,Samanta, Rajarshi
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supporting information
p. 5167 - 5171
(2018/09/13)
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- A method for synthesizing periodide (by machine translation)
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The invention discloses a method for synthesizing periodide, which belongs to the technical field of organic synthesis. The present invention is directed to the the periodide acrimony smell, volatile, toxicity is relatively large, and processing are not convenient, and the problem of low yield of the product, the present invention provides a method for synthesizing periodide. (by machine translation)
- -
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Paragraph 0005; 0009
(2017/03/18)
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- Method for preparing diazonium salt by utilizing micro-reactor
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The invention provides a method for preparing diazonium salt by utilizing a micro-reactor. The method comprises the following steps: firstly, preparing a nitrite solution and an organic amine into oil-water emulsion through a micro-mixer; enabling the oil-water emulsion to react with an introduced acid in a micro-channel to obtain the diazonium salt. The size of the salt formed by the contact of the oil-water emulsion and the acid is very small, and the salt can be consumed rapidly when reacting with nitrous acid, so that a pipeline is not blocked. The method provided by the invention is convenient and rapid to operate and short in reaction time; the defect that the diazonium salt is decomposed, caused by the fact that the temperature is too high, is avoided, and industrial production can be realized.
- -
-
Paragraph 0050; 0051
(2016/11/24)
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- Easy Access to Difluoromethylene-Containing Arene Analogues through Palladium-Catalysed C–H Olefination
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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
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supporting information
p. 5529 - 5538
(2016/11/25)
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- Rapid and efficient copper-catalyzed finkelstein reaction of (hetero)aromatics under continuous-flow conditions
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A general, rapid, and efficient method for the copper-catalyzed Finkelstein reaction of (hetero)aromatics has been developed using continuous flow to generate a variety of aryl iodides. The described method can tolerate a broad spectrum of functional groups, including N-H and O-H groups. Additionally, in lieu of isolation, the aryl iodide solutions were used in two distinct multistep continuous-flow processes (amidation and Mg-I exchange/nucleophilic addition) to demonstrate the flexibility of this method.
- Chen, Mao,Ichikawa, Saki,Buchwald, Stephen L.
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supporting information
p. 263 - 266
(2015/02/05)
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- Metal-free iodination of arylboronic acids and the synthesis of biaryl derivatives
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A simple, general and efficient method is developed for the metal-free iodination of arylboronic acids. The protocol uses very cheap molecular iodine as the halide source and potassium carbonate as the base. The method is highly tolerant of various functional groups present in the substrates. Importantly, the iodination strategy can also be applied very effectively in the one-pot, two-step synthesis of biaryl derivatives. Georg Thieme Verlag Stuttgart New York.
- Niu, Liting,Zhang, Hao,Yang, Haijun,Fu, Hua
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supporting information
p. 995 - 1000
(2014/05/06)
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- Iron-catalyzed cross-coupling reaction: Recyclable heterogeneous iron catalyst for selective olefination of aryl iodides in poly(ethylene glycol) medium
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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
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supporting information
p. 1030 - 1034
(2013/07/26)
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- A simple and effective copper catalyst for the conversion of arylboronic acids to aryl iodides at room temperature
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Simple Cu(NO3)2·3H2O was demonstrated to be of ability to catalyze the conversion of arylboronic acids to aryl iodides at room temperature. Compared with the previous copper-catalyzed method, the present procedure avoids the use of the ligand, the oxidant as well as the heating condition.
- Ren, Yun-Lai,Tian, Xin-Zhe,Dong, Chuanhua,Zhao, Shuang,Wang, Jianji,Yan, Mengjie,Qi, Xiaoguang,Liu, Guihua
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- Synthesis and structure-activity relationship of 5-substituent-2(1H)- pyridone derivatives as anti-fibrosis agents
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Pyridone compounds, such as pirfenidone (PFD) and fluorofenidone (AKF-PD), are multi-target anti-fibrotic agents. Using PFD and AKF-PD as the leading compounds, two series of novel (5-substituent)-2(1H)-pyridone compounds were synthesized with the purpose of maintaining multi-targeting property and overcoming the drawbacks of fast metabolism. These derivatives demonstrated good proliferation inhibiting activity against NIH3T3 cells by MTT assay with AKF-PD as the positive control. Compound 5b exhibited a high potent of anti-fibrosis with a IC50 of 0.08 mmol/L about 34 times of AKF-PD. The SAR of pyridone derivatives as anti-fibrosis agents was also discussed.
- Chen, Jun,Lu, Miao-Miao,Liu, Bin,Chen, Zhuo,Li, Qian-Bin,Tao, Li-Jian,Hu, Gao-Yun
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scheme or table
p. 2300 - 2302
(2012/04/18)
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- Synthesis of complex ortho-allyliodoarenes by employing the reductive iodonio-claisen rearrangement
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The reductive iodonio-Claisen rearrangement (RICR), involving complex aromatic λ3-iodanes and allyltrimethylsilane, was investigated. The RICR reaction of complex substituted aromatic hypervalent iodine (III) compounds and an allylmetal partner was conducted. The anionic oxy Cope rearrangement was found to be approximately 1010 to 1017 times faster than the neutral oxy Cope rearrangement due to weakening of the adjacent C-C bond by the oxygen anion. The results also indicate that the steric and electronic nature of the aromatic λ3-iodanes is the dominant factor influencing the [3,3]-sigmatropic rearrangement reaction. The removal of tert-butyl ether protecting group by using trifluroacetic acid in dichloromethane in the presence of triisopropylsilane gives the natural product broussin in 39% yield.
- Khatri, Hem Raj,Zhu, Jianglong
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p. 12232 - 12236
(2012/11/07)
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- PROCESS FOR THE PREPARATION OF IODIDES
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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 35
(2012/01/05)
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- Copper-catalyzed halogenation of arylboronic acids
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In this Letter, a copper-catalyzed halogenation of arylboronic acids was described. This reaction tolerates a variety of functional groups, providing aromatic halides with good yields. It represents a facile and mild procedure to aryl halides.
- Zhang, Guangyou,Lv, Guanglei,Li, Liping,Chen, Fan,Cheng, Jiang
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experimental part
p. 1993 - 1995
(2011/04/25)
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- Method for separating substances
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An objective of the present invention is to provide electrophoretic separation methods and devices that enable the various features of a substrate surface that comes in contact with an electrophoresis medium to be controlled. The present invention provides methods for electrophoresing substances, which comprises the steps of: (a) adding a substance to be analyzed to an electrophoresis medium retained in a substrate, whose surface that has come in contact with the electrophoresis medium has been coated with a polymer membrane; and (b) adding electrophoretic pressure to the electrophoresis medium. For example, the use of a plasma-polymerized membrane allows the formation of a membrane with homogeneous quality and thickness on the surface of an arbitrary shape. In addition, desired characteristics can be conferred on the surface through selection of monomeric substances. Protein adsorption onto micro-chips can be effectively prevented as well.
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- Halodediazoniations of dry arenediazonium o-benzenedisulfonimides in the presence or absence of an electron transfer catalyst. Easy general procedures to prepare aryl chlorides, bromides, and iodides
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The paper reports the results of a wide study aimed at preparing aryl chlorides 3 (19 examples), bromides 4 (19 examples), and iodides 5 (9 examples) by halodediazoniation of dry arenediazonium o-benzenedisulfonimides 1 with tetraalkylammonium halides 2. The reactions were carried out in anhydrous acetonitrile at room temperature (~20 °C) in the presence of copper powder and at 60 °C or room temperature without the catalyst. In optimal conditions the yields were from good to excellent (60 reactions, 61- 94% yield), with only a few exceptions (8 reactions, 51-55% yield). A good amount of the o-benzenedisulfonimide (7) was always recovered from the reactions and could then be reused to prepare salts 1. An interesting aspect of this research is the surprising role of the anion of o- benzenedisulfonimide (9) as an electron transfer agent.
- Barbero,Degani,Dughera,Fochi
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p. 3448 - 3453
(2007/10/03)
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- Oligomerization of (diacetoxyiodo)benzene with trifluoromethanesulfonic acid. Preparation and structure of hypervalent iodine oligomers
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(equation presented) Treatment of (diacetoxyiodo)benzene with an excess amount of trifluoromethanesulfonic acid (TfOH) gives hypervalent iodine oligomers after quenching by aqueous NaBr. The thermolysis by KI yielding p-diiodobenzene and iodobenzene indicates that the structure for the oligomers consists of p-phenylene unit. The iodine oligomers in situ generated react with aromatic substrates such as benzene, toluene, and chlorobenzene to give the corresponding arylated iodine oligomers.
- Kitamura, Tsugio,Wakimoto, Ichiro,Nakamura, Tetsu,Fujiwara, Yuzo
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p. 253 - 255
(2008/02/13)
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- The synthesis of [18F]fluoroarenes from the reaction of cyclotron-produced [18F]fluoride ion with diaryliodonium salts
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Diaryliodonium salts have been shown to react with fluoride ion at 80°C in acetonitrile to generate aryl fluorides. The regioselectivity is controlled electronically and by the bulk of the ortho-substituents on the rings, with the latter the dominant factor such that electron-rich rings can be fluorinated. ortho-Substituted aryl fluorides can be selectively produced from unsymmetrical diaryliodonium salts. The process has been used to synthesise [18F] labelled aromatics by the use of cyclotron generated [18F]fluoride ion.
- Shah, Aneela,Pike, Victor W.,Widdowson, David A.
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p. 2043 - 2046
(2007/10/03)
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- Low-temperature reactions of dihalogenosilylenes, SiX2, with I2 or ICl in toluene yielding dihalogenoiodo(methylphenyl)silanes
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The gaseous silylenes, SiX2 (X = F, Cl, Br or I), have been condensed into solutions of I2 or ICl in toluene at -90°C to give a range of new compounds of formula SiX2I(C6H4Me), demonstrating the generality of a type of reaction of silylenes first observed with SiO. All the products were mixtures of ortho, meta and para isomers but with an uncommonly high proportion of the ortho isomer in some cases. As the same iodosilane derivatives were obtained using I2 or ICl as reagents, it is proposed that the reactions involve electrophilic attack of silylium ions, SiX2I+, on the arene.
- Church, Simon R.,Davies, Christopher G.,Luemen, Regine,Mounier, Pierre A.,Saint, Gavin,Timms, Peter L.
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p. 227 - 230
(2007/10/03)
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- Simple anf Efficient Palladium-Catalyzed Carbonylation of Iodoxyarenes in Water under Mild Conditions
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Iodoxyarenes (ArIO2) readily react with CO (1 atm) in water, in the presence of Na2 (0.1percent) and Na2CO3 at 40-50 deg C, to give the corresponding carboxylic acids, ArCOOH, in 55-89percent isolated yield.Particulary attractive features of the reaction are that, unlike most iodoarenes, ArIO2 can be carbonylated in aqueous media without any organic solvents, due to their solubility in water and high reactivity.
- Grushin, Vladimir V.,Alper, Hovard
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p. 4794 - 4795
(2007/10/02)
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- THE IODINATION OF AROMATIC SUBSTRATES ON ALUMINA
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The iodination of a wide variety of aromatic substrates has been attained on dehydrated alumina.The procedure is particularly well suited for arenes.
- Boothe, Richard,Dial, Christopher,Conaway, Richard,Pagni, Richard M.,Kabalka, George W.
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p. 2207 - 2210
(2007/10/02)
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- Kinetics of Reduction of Phenyl Iodoso Acetates by L-Ascorbic Acid in Aqueous Acetic Acid: Structure Reactivity Study
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Kinetics of the reduction of various phenyl iodoso acetates (PIA) by L-ascorbic acid (H2A) have been studied in the presence of acetic acid with a view to finding out the effect of structure on the reactivity of PIA.The kinetic features, viz. first order dependence in , fractional in and linearity of the reciprocal plot /V versus 1/ etc, substantiate the Michaelis-Menten type of mechanism as well as the rate law to be opreative in all systems investigated.The rate constant follows the order: p-OCH3 > p-CH3 > m-CH3 > H > m-Cl > m-NO2 > p-Cl > p-Br > p-NO2.However, there is a marked deviation with para-substituents when the rate data (k) are fit in Hammett's equation.Thermodynamic parameters have been calculated.The isokinetic temperature (β = 260 K) is below the experimental temperature (295-320 K) indicating the reaction to be entropy controlled.
- Saiprakash, P. K.,Rajanna, K. Chinna,Devi, Y. Uma
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p. 292 - 294
(2007/10/02)
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- Regiospecific Synthesis of Aryl(2-furyl)iodonium Tosylates, a New Class of Iodonium Salts, from arenes and 2-(Trimethylsilyl)furans in Organic Solvents
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The treatment of 2,5-bis(trimethylsilyl)furan with various arenes (ArI(OH)OTs) in acetonitrile/ methanol has been found to give aryliodonium tosylates in yields ranging from 62percent to 80percent.With 2-methyl-5-(trimethylsilyl)furan as the substrate, aryl(5-methyl-2-furyl)iodonium tosylates are likewise obtained in yields ranging from 61percent to 74percent.The reactions of arenes with 2-(trimethylsilyl)furan in methanol give aryl(2-furyl)iodonium tosylates in much lower yield (9-23percent) and are accompanied by the reductive decomposition of the hypervalent organoiodine component.To our knowledge, these are the first reported examples of aryl(furyl)iodonium salts.
- Carman, Carol S.,Koser, Gerald F.
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p. 2534 - 2539
(2007/10/02)
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- Polar Radicals. 17. On the Mechanism of Iodine Atom Transfer. A 9-I-2 Intermediate
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The atom-transfer reaction of iodine from an aryl iodide to a phenyl radical has been shown to proceed via a 9-I-2 ntermediate.The relative kinetics of the reactions of the intermediate were investigated by studying its mode of decomposition upon formation from the reduction of a series of unsymmetrically substituted diaryliodonium salts.The iodonium salts were reduced by the electron-transfer reactions with several reagents: di-tert-butyl nitroxide, sodium 2,6-di-tert-butylphenylate, and sodium phenylate.The reduction by electron transfer of the iodonium salts by the latter reaction gives high yields of diaryl ethers.The mechanism fo ether formation has been shown to proceed by two mechanistic pathways.For the diaryliodonium salts that have a p-cyano or p-nitro substituent, the ether is formed by a nucleophilic aromatic substitution; however, when the substituents were not strongly electron withdrawing, the mechanism resulting in ether formation involved electron transfer from the phenylate anion to the iodonium salt to form the phenoxy radical and a 9-I-2 intermediate.The intermediate decomposes to an aryl radical and an aryl iodide.The ether is formed from the efficient coupling of the aryl radical and the phenoxy radical.
- Tanner, Dennis D.,Reed, Darwin W.,Setiloane, B.P.
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p. 3917 - 3923
(2007/10/02)
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- Ortho Lithiations of Arenesulfonic Acids. New Methodology for Electrophilic Aromatic Substitutions
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The directed ortho lithiation of aromatic sulfonic acids occurs in high yield.The ease of desulfonation makes this a useful method for the synthesis of substituted arenes lacking the sulfonic acid function.
- Figuly, Garret D.,Martin, J. C.
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p. 3728 - 3729
(2007/10/02)
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- Aryl Radical Departure Aptitudes in Reactions of Diaryliodonium Fluoroborates with Sodium Ethoxide
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Several unsymmetrical diaryliodonium fluoroborates have been prepared and subjected to reaction with sodium ethoxide in ethanol solution at 71 deg C.From quantitative determinations of products, it has been possible to calculate apparent departure aptitudes of several common aryl radical cations of type 6.These results are compared with similar data obtained from thermolysis reactions of hydroxytetraarylstiboranes.
- Lubinkowski, Jacek J.,Arrieche, Cecilia Gimenez,McEwen, William E.
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p. 2076 - 2079
(2007/10/02)
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- Reactivities of Several Nucleophiles toward 4-Methylbenzyne in Very Hot Water
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By means of competition experiments, the relative rates of reaction of several nucleophiles with 4-methylbenzyne in aqueous solution at temperatures up to 318 deg C have been determined.The relative nucleophilicities vs. chloride ion are as follows: PhS-, 46; I-, 6.2; piperidine, 3.0; Br-, 1.7; aniline, 1.3; Cl-, (1.0); PhO-, 1.0; ammonia, 0.55; F-, 0.20.For all but PhS-, piperidine, and iodide, the p/m product ratio is 0.83+/-0.02.In the cases of PhS- and piperidine a competing mechanism of ipso substitution, probably involving catalysis by copper ions, caused the observed p/m ratios to be high and variable.Our experimental design precluded determination of the p/m ratio for iodide ion.Because of chemical complications, only rough estimates could be made of the nucleophilicities of nitrite and benzenesulfinate ions.
- Zoratti, Mario,Bunnett, J. F
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p. 1776 - 1782
(2007/10/02)
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- Mechanism of the Non-Aryne Hydroxydehalogenation of Unactivated Aryl Halides
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The hydroxydehalogenation of aryl halides upon reaction with aqueous alkali at temperatures up to 333 deg C was examined to determine the nature of an ipso hydroxydehalogenation process reported in 1957 to compete with the aryne mechanism.The reactions of p-iodo-, p-bromo-, and p-chlorotoluene with aqueous solutions of sodium or potassium hydroxide or carbonate, carried out in Pyrex glass tubes with exclusion of traces of transition metals, led in all cases to the same product distribution. m-Cresol and p-cresol, the two main products, formed with a para/meta ratio of0.82+/-0.03, consistent with the occurence of the aryne mechanism only.Addition of traces of copper salts or conducting the reaction in a Monel bomb, as done by other investigators, caused the occurence of a non-aryne ipso hydroxydehalogenation.This effect was not produced by nickel, iron, manganese, or cadmium.The ipso hydroxydehalogenation observed in previous studies is identified as a copper-catalyzed process.
- Zoratti, Mario,Bunnett, J. F.
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p. 1769 - 1776
(2007/10/02)
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