- A new method of introducing a trifluoromethyl group into an aromatic ring
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Trifluoromethyl derivatives of aromatic molecules were prepared from aromatic halides, converted to dithiocarboxylic acids through formation of Grignard reagents, followed by fluorination with xenon difluoride at room temperature.
- Zupan, Marko,Bregar, Zvonko
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Read Online
- Cross-Coupling through Ag(I)/Ag(III) Redox Manifold
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In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.
- Demonti, Luca,Mézailles, Nicolas,Nebra, Noel,Saffon-Merceron, Nathalie
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supporting information
p. 15396 - 15405
(2021/10/12)
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- Photoredox catalysis on unactivated substrates with strongly reducing iridium photosensitizers
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Photoredox catalysis has emerged as a powerful strategy in synthetic organic chemistry, but substrates that are difficult to reduce either require complex reaction conditions or are not amenable at all to photoredox transformations. In this work, we show that strong bis-cyclometalated iridium photoreductants with electron-rich β-diketiminate (NacNac) ancillary ligands enable high-yielding photoredox transformations of challenging substrates with very simple reaction conditions that require only a single sacrificial reagent. Using blue or green visible-light activation we demonstrate a variety of reactions, which include hydrodehalogenation, cyclization, intramolecular radical addition, and prenylationviaradical-mediated pathways, with optimized conditions that only require the photocatalyst and a sacrificial reductant/hydrogen atom donor. Many of these reactions involve organobromide and organochloride substrates which in the past have had limited utility in photoredox catalysis. This work paves the way for the continued expansion of the substrate scope in photoredox catalysis.
- Shon, Jong-Hwa,Kim, Dooyoung,Rathnayake, Manjula D.,Sittel, Steven,Weaver, Jimmie,Teets, Thomas S.
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p. 4069 - 4078
(2021/04/06)
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- An Efficient Deprotection of 2,6-Bis(trifluoromethyl)phenylboronic Esters via Catalytic Protodeboronation Using Tetrabutyl ammonium Fluoride
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We herein describe an efficient deprotection of 2,6-bis(trifluoromethyl)phenylboronic esters, which serve as effective protective groups for 1,2- or 1,3-diols in various organic transformations, via protodeboronation by using a catalytic amount of tetrabutylammonium fluoride (TBAF).
- Makino, Kazuishi,Nojima, Shinya,Shimada, Naoyuki,Urata, Sari
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supporting information
p. 2300 - 2304
(2019/12/11)
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- Synthesis and Characterization of Strong Cyclometalated Iridium Photoreductants for Application in Photocatalytic Aryl Bromide Hydrodebromination
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A series of potent bis-cyclometalated iridium photoreductants with electron-rich β-diketiminate (NacNac) ancillary ligands is described. Structure-property analysis reveals that substituent modification of the NacNac ligands has a large effect on the ground-state IrIV/IrIII potential, which shifts cathodically as the NacNac is made more electron-rich. In addition, the excited-state IrIV/?IrIII potentials are ca. 300-500 mV more negative than that of fac-Ir(ppy)3 (ppy = 2-phenylpyridine), indicating that these compounds have much more reducing excited states. Rate constants for excited-state electron transfer between these photosensitizers and benzophenone are -2-3 times faster than fac-Ir(ppy)3, demonstrating that these complexes are both kinetically and thermodynamically more potent for excited-state electron transfer. We use these photosensitizers to optimize a simple reaction procedure for photocatalytic debromination of aryl bromide substrates, which requires only the photosensitizer, blue light, and an amine base, without silanes or other additives that are used in previously reported methods.
- Shon, Jong-Hwa,Sittel, Steven,Teets, Thomas S.
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p. 8646 - 8658
(2019/09/12)
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- Visible-Light photoredox decarboxylation of perfluoroarene iodine(III) Trifluoroacetates for C-H trifluoromethylation of (Hetero)arenes
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A scalable and operationally simple decarboxylative trifluoromethylation of (hetero)arenes with easily accessible C6F5I(OCOCF3)2 under photoredox catalysis has been developed. This method is tolerant of various (hetero)arenes and functional groups. Notably, C6F5I is recycled from the decarboxylation reaction and further used for the preparation of C6F5I(OCOCF3)2. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the application of trifluoroacetic acid in trifluoromethylation reactions.
- Yang, Bin,Yu, Donghai,Xu, Xiu-Hua,Qing, Feng-Ling
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p. 2839 - 2843
(2018/04/14)
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- Palladium-mediated radical homocoupling reactions: A surface catalytic insight
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In this contribution, we report a palladium nanoparticle-promoted reductive homocoupling of haloarenes that proceeds efficiently to produce corresponding bis-aryls in moderate to excellent yields using relatively low catalyst loading (1 mol%), and exhibits broad functional group tolerance. This work sheds light on how the surface state of Pd(0) nanoparticles plays a crucial role in the reactivity of catalytic systems. Notably, the appropriate choice of palladium salts for the preparation of the preformed nanocatalysts was a key parameter having a major impact on the catalytic activity; thus, the effect of halide anions on the reactivity of the as-prepared palladium nanoparticles could be assessed, with iodide anions being capable of inhibiting the corresponding homocoupling reaction. The homocoupling reaction mechanism has been further studied by means of radical trap and electron paramagnetic resonance (EPR) experiments, revealing that the reaction proceeds via radical intermediates. Taking into account these data, a plausible reaction mechanism based on single-electron transfer processes on the palladium nanoparticle surface is discussed.
- Favier, Isabelle,Toro, Marie-Lou,Lecante, Pierre,Pla, Daniel,Gómez, Montserrat
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p. 4766 - 4773
(2018/09/29)
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- Catalytic Reduction of Alkyl and Aryl Bromides Using Propan-2-ol
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Milstein's complex, (PNN)RuHCl(CO), catalyzes the efficient reduction of aryl and alkyl halides under relatively mild conditions by using propan-2-ol and a base. Sterically hindered tertiary and neopentyl substrates are reduced efficiently, as well as more functionalized aryl and alkyl bromides. The reduction process is proposed to occur by radical abstraction/hydrodehalogenation steps at ruthenium. Our research represents a safer and more sustainable alternative to typical silane, lithium aluminium hydride, and tin-based conditions for these reductions.
- Haibach, Michael C.,Stoltz, Brian M.,Grubbs, Robert H.
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supporting information
p. 15123 - 15126
(2017/11/20)
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- Base-Catalyzed Aryl-B(OH)2 Protodeboronation Revisited: From Concerted Proton Transfer to Liberation of a Transient Aryl Anion
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Pioneering studies by Kuivila, published more than 50 years ago, suggested ipso protonation of the boronate as the mechanism for base-catalyzed protodeboronation of arylboronic acids. However, the study was limited to UV spectrophotometric analysis under acidic conditions, and the aqueous association constants (Ka) were estimated. By means of NMR, stopped-flow IR, and quenched-flow techniques, the kinetics of base-catalyzed protodeboronation of 30 different arylboronic acids has now been determined at pH > 13 in aqueous dioxane at 70 °C. Included in the study are all 20 isomers of C6HnF(5-n)B(OH)2 with half-lives spanning 9 orders of magnitude: a and Sδ values, kinetic isotope effects (2H, 10B, 13C), linear free-energy relationships, and density functional theory calculations, we have identified a mechanistic regime involving unimolecular heterolysis of the boronate competing with concerted ipso protonation/C-B cleavage. The relative Lewis acidities of arylboronic acids do not correlate with their protodeboronation rates, especially when ortho substituents are present. Notably, 3,5-dinitrophenylboronic acid is orders of magnitude more stable than tetra-and pentafluorophenylboronic acids but has a similar pKa.
- Cox, Paul A.,Reid, Marc,Leach, Andrew G.,Campbell, Andrew D.,King, Edward J.,Lloyd-Jones, Guy C.
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supporting information
p. 13156 - 13165
(2017/09/26)
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- Aryl(triethyl)silanes for Biaryl and Teraryl Synthesis by Copper(II)-Catalyzed Cross-Coupling Reaction
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Aryl(triethyl)silanes are found to undergo cross-coupling with iodoarenes in the presence of catalytic amounts of CuBr2and Ph-Davephos, as well as cesium fluoride as a stoichiometric base. Because the silicon reagents are readily accessible through catalytic C?H silylation of aromatic substrates, the net transformation allows coupling of aromatic hydrocarbons with iodoarenes via triethylsilylation.
- Komiyama, Takeshi,Minami, Yasunori,Hiyama, Tamejiro
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supporting information
p. 15787 - 15791
(2016/12/16)
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- Study on the degradation of the highly reactive hypervalent trifluoromethylation iodine reagent PhI(OAc)(CF3)
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Degradation of the highly reactive hypervalent trifluoromethylation iodine reagent PhI(OAc)(CF3), which can only be generated in situ with mixing PhI(OAc)2 and TMSCF3 in the presence of CsF, was studied by ESI-MS and GC-MS combined with 19F-NMR. The important transient intermediate PhICF3+ was determined by ESI-MS, and the major volatile products containing CF3 were identified with the authentic compounds by using GC-MS, such as trifluoromethylbenzene, 2-iodobenzotrifluoride, 3-iodobenzotrifluoride, 4-iodobenzotrifluoride. Meanwhile, more evidences obtained with 19F-NMR were given for such degradation reaction. A possible rapid CF3 radical transfer reaction pathway was proposed to clarify such degradation progress based on the experimental results. Therefore, this study may be helpful in elucidating the intrinsic reactivity of PhI(OAc)(CF3) and the possible competing side reactions caused by such self-degradation pathway. Degradation of the highly reactive hypervalent trifluoromethylation iodine reagent PhI(OAc)(CF3), which can only be generated in situ with mixing PhI(OAc)2 and TMSCF3 in the presence of CsF, was studied by ESI-MS and GC-MS combined with 19F-NMR. The important transient intermediate PhICF3+ was determined by ESI-MS, and the major volatile products containing CF3 were identified with the authentic compounds by using GC-MS, such as trifluoromethylbenzene, 2-iodobenzotrifluoride, 3-iodobenzotrifluoride, 4-iodobenzotrifluoride. Meanwhile, more evidences obtained with 19F-NMR were given for such degradation reaction. A possible rapid CF3 radical transfer reaction pathway was proposed to clarify such degradation progress based on the experimental results. Therefore, this study may be helpful in elucidating the intrinsic reactivity of PhI(OAc)(CF3) and the possible competing side reactions caused by such self-degradation pathway.
- Zhu, Hui,Zhang, Shusheng,Wang, Haoyang,Xu, Bin,Guo, Yinlong
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supporting information
p. 1365 - 1370
(2016/02/18)
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- Examples of catalytic and selective routes for fluorinated building blocks
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Examples are presented for the catalytic fluorination of chlorinated starting materials in order to produce building blocks or HFCs. The fluorination of CF3CH2Cl, of CCl2=CCl2, of trichloromethoxylbenzenes and trichloromethoxybenzene involving nucleophilic substitution are reported. In all cases, HF was the fluorinating agent. Depending on the chlorinated substrate and the degree of fluorination required, liquid- or gas-phase processes were involved. Usually, catalysts were SbCl 5 in liquid phase and chromium oxide in gas phase. In the presence of SbCl5, at 90 °C under an initial pressure of 10 bar, the fluorination of CCl2=CCl2 leads mainly to the formation of CClF2CHCl2, and the active catalyst is an antimony mixed halide (SbCl3F2). In the same way, the presence of SbCl5 favored the formation of 1-trifluoromethyl-3- trichloromethylbenzene from bis-1,3-trichloromethylbenzene at low temperature (50 °C) and in the presence of a low amount of HF. Moreover, trichloromethoxybenzene was totally transformed into trifluoromethoxybenzene. At 380 °C and at atmospheric pressure, the transformation of CF 3CH2Cl into CF3CH2F was favored over chromium oxide-based catalyst modified by zinc (corresponding to a (Zn/Zn + Cr) molar ratio of 0.22).
- Brunet, Sylvette
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p. 1067 - 1071
(2014/11/27)
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- Base-promoted protodeboronation of 2,6-disubstituted arylboronic acids
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Facile based promoted deboronation of electron-deficient arylboronate esters was observed for arylboronates containing two ortho electron-withdrawing group (EWG) substituents. Among 30 representative boronates, only the diortho-substituted species underwe
- Lozada, Jerome,Liu, Zhibo,Perrin, David M.
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supporting information
p. 5365 - 5368
(2014/06/23)
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- DIRECT TRIFLUOROMETHYLATIONS USING TRIFLUOROMETHANE
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A direct trifluoromethylation method preferably using a trifluoromethane as a fluoro-methylating species. In particular, the present method is used for preparing a trifluoromethylated substrate by reacting a fluoromethylatable substrate with a trifiuoromethylating agent in the presence of an alkoxide or metal salt of silazane under conditions sufficient to trifluoromethylate the substrate; wherein the fluoromethylatable substrate includes chlorosilanes, carbonyl compounds such as esters, aryl halides, aldehydes, ketones, chalcones, alkyl formates, alkyl halides, aryl halides, alkyl borates, carbon dioxide or sulfur.
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Paragraph 0049
(2014/03/25)
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- Palladium catalytic systems with hybrid pyrazole ligands in C-C coupling reactions. Nanoparticles versus molecular complexes
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This paper reports the comparison of the chemoselectivity of two different Pd catalytic systems, namely molecular and colloidal systems, in C-C coupling reactions. For this purpose, new hybrid pyrazole derived ligands containing alkylether, alkylthioether or alkylamino moieties have been synthesized and used to form Pd(ii) complexes and to stabilize Pd nanoparticles (Pd NPs). With the aim of studying the coordination mode of the ligands and further to understand their role in catalysis, both types of Pd species were characterized by appropriate techniques. In C-C coupling reactions promoted by different Pd colloidal systems, several reports evidenced that active species are molecular catalysts leached from Pd NPs. The most important feature of this work relies on the differences observed in the output of C-C coupling reactions, depending on the colloidal or molecular nature of the catalyst employed. Thus, molecular systems carry out typical Suzuki-Miyaura cross-coupling, together with the dehalogenation of the substrate in different proportions. In contrast, Pd NPs catalyze either Suzuki-Miyaura or C-C homocoupling reactions depending on the haloderivative used. Interestingly, Pd NPs catalyze the quantitative dehalogenation of 4-iodotoluene. Differences observed in the chemoselectivity of these two catalytic systems support that reactions carried out with Pd NPs stabilized with the hybrid pyrazole ligands employed here take place on the surface of the colloids. The Royal Society of Chemistry 2013.
- Peral, Daniel,Gomez-Villarraga, Fernando,Sala, Xavier,Pons, Josefina,Carles Bayon,Ros, Josep,Guerrero, Miguel,Vendier, Laure,Lecante, Pierre,Garcia-Anton, Jordi,Philippot, Karine
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p. 475 - 489
(2013/03/14)
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- Arylsulfur chlorotetrafluorides as useful fluorinating agents: Deoxo- and dethioxo-fluorinations
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Usage of arylsulfur chlorotetrafluorides 1 as versatile deoxo- and dethioxo-fluorinating agents is described. There have been developed two convenient methods for the in situ preparation of reactive arylsulfur trifluorides 2 from 1. The one is reduction of 1 with a reducer such as pyridine to 2, and the other is disproportionation of 1 with a diaryl disulfide to 2 with evolution of chlorine gas. The latter method is a convenient way to get neat 2 from 1. The in situ prepared 2 fluorinates many kinds of substrates such as alcohols, aldehydes, ketones, diketones, and carboxylic acids to give the corresponding CF, CF2, CF2CF2, and CF 3 compounds in high yields. 2 also fluorinates various sulfur compounds including CS groups to give CF2, OCF2, CF 3, and OCF3 compounds in high yields. Reactions of 2 with diols or bis(trimethylsilyl) derivatives of diols or amino alcohols provided the corresponding deoxofluoro-arylsulfinylation products in high yields. In addition, it has been found that chlorotetrafluorides 1 directly and effectively react with the sulfur compounds to give the corresponding fluoro compounds in high yields. Since they are the intermediates for the production of industrially useful arylsulfur pentafluorides, arylsulfur chlorotetrafluorides 1, in particular, phenylsulfur chlorotetrafluoride (1a) are expected to find use as inexpensive and versatile deoxo- and dethioxo-fluorinating agents for the preparation of many organofluoro compounds.
- Umemoto, Teruo,Singh, Rajendra P.
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experimental part
p. 17 - 27
(2012/09/07)
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- Palladium(II)-catalyzed coupling of electron-deficient arenes via C-H activation
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Homocoupling and cross-coupling of electron-deficient arenes, including nitrobenzene, (trifluoromethyl)benzene, ethyl benzoate, etc., have been developed to afford biaryls using a catalytic system of Pd(OAc) 2/trifluoroacetic acid (TFA)/O2 or K2S 2O8. The crucial step is to tune the concentrations of arenes and the loading of TFA carefully to enhance the reaction rates and the selectivity of these couplings involving dual C-H activation.
- Zhou, Lihong,Lu, Wenjun
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scheme or table
p. 2124 - 2127
(2012/06/01)
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- Rhodium(I)-catalyzed synthesis of aryltriethoxysilanes from arenediazonium tosylate salts with triethoxysilane
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An efficient method for the preparation of aryltriethoxy-silanes from arenediazonium tosylate salts has been developed, which expands the substrates of rhodium-catalyzed silylation from iodides, bromides, and triflates to diazonium salts. A new method for hydrodediazoniation has also been explored.
- Tang, Zhi Yong,Zhang, Yuan,Wang, Tao,Wang, Wei
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supporting information; experimental part
p. 804 - 808
(2010/06/14)
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- METHODS AND COMPOSITIONS FOR PRODUCING DIFLUOROMETHYLENE-AND TRIFLUOROMETHYL-CONTAINING COMPOUNDS
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New methods for producing difluoromethylene-containing compounds with phenylsulfur trifluoride or a primary alkyl-substituted phenylsulfur trifluoride are disclosed. Also, new methods for producing trifluoromethyl-containing compounds with phenylsulfur trifluoride or primary alkyl-substituted phenylsulfur trifluoride are also disclosed.
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Page/Page column 31-32
(2009/07/17)
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- The first catalytic method for Heck alkynylation of unactivated aryl bromides (copper-free Sonogashira) in an ionic liquid: 1 mol-% palladium/triphenylphosphane/pyrrolidine in [BMIM][BF4] as a simple, inexpensive and recyclable system
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Herein we report the studies of Heck alkynylation (copper-free Sonogashira) with aryl halides (I, Br, Cl) employing various metallic precursors, tertiary phosphanes and bases in [BMIM][BF4] as the solvent. As a result, we provide the first method that allows the coupling of a large array of substrates, either activated or deactivated bromides in an ionic liquid. Furthermore, the system of highest efficiency is unexpectedly the simplest and cheaper combination that employs [Pd(η3-C3H 5)Cl]2/PPh3 at only a 1 mol-% loading with pyrrolidine as the base and in the absence of a copper salt. The coupling of sterically and electronically deactivated bromides bearing different functional groups to aryl- and alkyl acetylenes, as well as the possibility of recycling, make these results of high interest to the future development of Heck-and Sonogashira-type reactions in ionic liquids. Wiley-VCH Verlag GmbH & Co. KGaA.
- Hierso, Jean-Cyrille,Boudon, Julien,Picquet, Michel,Meunier, Philippe
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p. 583 - 587
(2007/10/03)
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- A superior method for the reduction of secondary phosphine oxides
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(Chemical Equation Presented) Diisobutylaluminum hydride (DIBAL-H) and triisobutylaluminum have been found to be outstanding reductants for secondary phosphine oxides (SPOs). All classes of SPOs can be readily reduced, including diaryl, arylalkyl, and dialkyl members. Many SPOs can now be reduced at cryogenic temperatures, and conditions for preservation of reducible functional groups have been found. Even the most electron-rich and sterically hindered phosphine oxides can be reduced in a few hours at 50-70°C. This new reduction has distinct advantages over existing technologies.
- Busacca, Carl A.,Lorenz, Jon C.,Grinberg, Nelu,Haddad, Nizar,Hrapchak, Matt,Latli, Bachir,Lee, Heewon,Sabila, Paul,Saha, Anjan,Sarvestani, Max,Shen, Sherry,Varsolona, Richard,Wei, Xudong,Senanayake, Chris H.
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p. 4277 - 4280
(2007/10/03)
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- Process for preparing fluorine-containing benzaldehydes
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The invention relates to a particularly advantageous preparation of fluorine-containing benzaldehydes by reacting a corresponding aromatic acid chloride with hydrogen in the presence of a supported palladium catalyst and a catalyst moderator.
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- Process for lithiation of 1,3-bis(trifluoromethyl)benzene
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A novel process for the lithiation of 1,3-bis(trifluoro-methyl)benzene in a solvent is described, said process comprising carrying out the lithiation with the lithium salt of an amine of the general formula wherein R1 and R2 are secondary or tertiary lower alkyl or secondary or tertiary lower alkyl substituted by a lower alkyl or lower cycloalkyl or lower cycloaklyl substituted by a lower alkyl, or R1 and R2 taken together form a C6-14 -alkylene group in which the two carbon atoms linked with the nitrogen atom are secondary or tertiary and are separated from each other by 2 to 4 carbon atoms. The solution of the lithiated 1,3-bis(trifluoromethyl)-benzene obtained can be reacted with an electrophile which is suitable for the substitution of lethiated benzene derivatives, whereby a compound of the formula STR1 wherein R3 signifies the residue of an electrophile which is suitable for the substitution of lithiated benzene derivatives, is obtained.
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- TRIFLUORMETHYLIERUNGSREAKTIONEN VON Te(CF3)2 MIT HALOGENBENZOLEN UND METHYLBENZOLEN
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Substituent effects on yields and regioselectivity of photochemical and thermal trifluoromethylation reactions of Te(CF3)2 with halogen benzenes and methyl benzenes are investigated under comparable conditions.All reactions lead to trifluoromethylated products.The yields of the thermal are always higher than those of the corresponding photochemical reactions.The reactivity of the halobenzenes increases in the series C6H5-F a sidereaction, but H-substitution is the primary reaction pathway.During the reactions with iodobenzene tellurium containing compounds are also formed.The reactions with methyl benzenes show an increase in reactivity in the series hexamethylbenzene mesitylene toluene p-xylene.In all cases only ring substituted products are detected.Reactions with toluene and p-xylene yield tellurium containing compounds as well as addition products.The 19F-n.m.r spectra of the products are given.
- Naumann, Dieter,Kischkewitz, Jurgen
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p. 283 - 299
(2007/10/02)
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- Sodium Perfluoroalkane Carboxylates as Sources of Perfluoroalkyl Groups
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Sodium trifluoroacetate, in the presence of copper(I) iodide, is used as a source of trifluoromethyl to replace halogen by trifluoromethyl in benzenoid and heterocyclic aromatic systems, as well as in alkenyl and alkyl halogen compounds.The mechanism of this interesting copper-assisted process has been explored and an intermediate of the form - is proposed.Introduction of higher perfluoroalkyl groups from their respective sodium perfluoroalkane carboxylates has been demonstrated and the machanistic features are compared with those of the trifluoromethylation process.
- Carr, Gillian E.,Chambers, Richard D.,Holmes, Thomas F.,Parker, David G.
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p. 921 - 926
(2007/10/02)
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- REACTIONS IN ANHYDROUS HYDROGEN FLUORIDE
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Anhydrous hydrogen fluoride serves as an excellent agent for introducing fluorine into organic compounds, as a solvent and a catalyst with Friedel-Crafts activity.A number of chlorine/fluorine exchange reactions which occur in HF are described, some of which have involved surprising rearrangement processes.New reactions, in which the catalytic action of hydrogen fluoride are utilized, are also discussed.
- Baasner, B.,Klauke, E.
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p. 553 - 564
(2007/10/02)
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