- Visible-Light-Enabled Carboxylation of Benzyl Alcohol Derivatives with CO2 Using a Palladium/Iridium Dual Catalyst
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A highly efficient carboxylation of benzyl alcohol derivatives with CO2 using a palladium/iridium dual catalyst under visible-light irradiation was developed. A wide range of benzyl alcohol derivatives could be employed to provide benzylic carboxylic acids in moderate to high yields. Mechanistic studies indicated that the oxidative addition of benzyl alcohol derivatives was possibly the rate-determining-step. It was also found that a switchable site-selective carboxylation between benzylic C?O and aryl C?Cl moieties could be achieved simply by changing the palladium catalyst.
- Iwasawa, Nobuharu,Jin, Yushu,Toriumi, Naoyuki
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- Suppressing carboxylate nucleophilicity with inorganic salts enables selective electrocarboxylation without sacrificial anodes
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Although electrocarboxylation reactions use CO2as a renewable synthon and can incorporate renewable electricity as a driving force, the overall sustainability and practicality of this process is limited by the use of sacrificial anodes such as magnesium and aluminum. Replacing these anodes for the carboxylation of organic halides is not trivial because the cations produced from their oxidation inhibit a variety of undesired nucleophilic reactions that form esters, carbonates, and alcohols. Herein, a strategy to maintain selectivity without a sacrificial anode is developed by adding a salt with an inorganic cation that blocks nucleophilic reactions. Using anhydrous MgBr2as a low-cost, soluble source of Mg2+cations, carboxylation of a variety of aliphatic, benzylic, and aromatic halides was achieved with moderate to good (34-78%) yields without a sacrificial anode. Moreover, the yields from the sacrificial-anode-free process were often comparable or better than those from a traditional sacrificial-anode process. Examining a wide variety of substrates shows a correlation between known nucleophilic susceptibilities of carbon-halide bonds and selectivity loss in the absence of a Mg2+source. The carboxylate anion product was also discovered to mitigate cathodic passivation by insoluble carbonates produced as byproducts from concomitant CO2reduction to CO, although this protection can eventually become insufficient when sacrificial anodes are used. These results are a key step toward sustainable and practical carboxylation by providing an electrolyte design guideline to obviate the need for sacrificial anodes.
- Corbin, Nathan,Lazouski, Nikifar,Manthiram, Karthish,Steinberg, Katherine,Yang, Deng-Tao
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p. 12365 - 12376
(2021/10/08)
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- Macrolactam Synthesis via Ring-Closing Alkene-Alkene Cross-Coupling Reactions
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Reported herein is a practical method for macrolactam synthesis via a Rh(III)-catalyzed ring closing alkene-alkene cross-coupling reaction. The reaction proceeded via a Rh-catalyzed alkenyl sp2 C-H activation process, which allows access to macrocyclic molecules of different ring sizes. Macrolactams containing a conjugated diene framework could be easily prepared in high chemoselectivities and Z,E stereoselectivities.
- Goh, Jeffrey,Loh, Teck-Peng,Maraswami, Manikantha
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supporting information
p. 9724 - 9728
(2020/12/21)
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- Pd(OH)2/C, a Practical and Efficient Catalyst for the Carboxylation of Benzylic Bromides with Carbon Monoxide
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A simple, efficient, cheap, and broadly applicable system for the carboxylation of benzylic bromides with carbon monoxide and water is reported. Upon simple reaction with only 2.5 wt % of Pearlman's catalyst and 10 mol % of tetrabutylammonium bromide in tetrahydrofuran at 110 °C for 4 h, a range of benzylic bromides can be smoothly converted to the corresponding arylacetic acids in good to excellent yields after simple extraction and acid-base wash. The reaction was found to be broadly applicable, scalable, and could be successfully extended to the use of ex situ-generated carbon monoxide and applied to the synthesis of the nonsteroidal anti-inflammatory drug diclofenac.
- Wakuluk-Machado, Anne-Marie,Dewez, Damien F.,Baguia, Hajar,Imbratta, Miguel,Echeverria, Pierre-Georges,Evano, Gwilherm
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p. 713 - 723
(2020/02/04)
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- Carboxylation of benzylic and aliphatic C-H bonds with CO2 induced by light/ketone/nickel
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A photoinduced carboxylation reaction of benzylic and aliphatic C-H bonds with CO2 is developed. Toluene derivatives capture gaseous CO2 at the benzylic position to produce phenylacetic acid derivatives when irradiated with UV light in the presence of an aromatic ketone, a nickel complex, and potassium tert-butoxide. Cyclohexane reacts with CO2 to furnish cyclohexanecar-boxylic acid under analogous reaction conditions. The present photoinduced carboxylation reaction provides a direct access from readily available hydrocarbons to the corresponding carboxylic acids with one carbon extension.
- Ishida, Naoki,Masuda, Yusuke,Imamura, Yuuya,Yamazaki, Katsushi,Murakami, Masahiro
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supporting information
p. 19611 - 19615
(2019/12/24)
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- Electrogenerated Sm(II)-Catalyzed CO2 Activation for Carboxylation of Benzyl Halides
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Sm(II)-catalyzed carboxylation of benzyl halides is reported through the electrochemical reduction of CO2. The transformation proceeds under mild reaction conditions to afford the corresponding phenylacetic acids in good to excellent yields. This user-friendly and operationally simple protocol represents an alternative to traditional strategies, which usually proceeds through the C(sp3)-halide activation pathway.
- Bazzi, Sakna,Schulz, Emmanuelle,Mellah, Mohamed
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supporting information
p. 10033 - 10037
(2019/12/24)
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- Preparation method of phenylacetic acid type compound
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The invention discloses a preparation method of a phenylacetic acid type compound. The preparation method of the phenylacetic acid type compound I comprises the following steps that in a solvent and aCO gas phase system, a benzyl halide type compound II, pyridine-2-cobalt carboxylate, palladium acetate and alkaline neutralizers take carbonylation reaction to obtain the phenylacetic acid type compound I. A mixed catalytic system has a synergistic effect; the whole use quantity of catalysts is greatly reduced. When the mixed catalyst is used, a better catalytic effect can be achieved; the characteristics of easily obtaining the catalyst, avoiding the production safety risk of toxic three wastes and the like, reducing the reaction pressure, realizing mild reaction conditions, reducing the production risk, facilitating the production and the like are realized. The formulas are shown in description.
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Paragraph 0107; 0108; 0109
(2019/02/21)
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- An improved method for the synthesis of phenylacetic acid derivatives via carbonylation
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2,4-Dichlorophenylacetic acid is synthesized in high yield via the carbonylation of 2,4-dichlorobenzyl chloride, and various experimental conditions are evaluated. Xylene, bistriphenylphosphine palladium dichloride, tetraethylammonium chloride and sodium hydroxide in solution are added to the reaction system and held at 80 °C under a CO atmosphere. 2,4-Dichlorophenylacetic acid is obtained in a maximum yield of 95percent, and a mechanism for 2,4-dichlorobenzyl chloride carbonylation is proposed. The reaction system provides a mild, effective and novel means by which to prepare phenylacetic acid derivatives from their corresponding benzyl chloride derivatives.
- Li, He,Zhang, Yijun,Liu, Dinghua,Liu, Xiaoqin
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p. 548 - 552
(2019/11/13)
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- Visible-Light-Driven External-Reductant-Free Cross-Electrophile Couplings of Tetraalkyl Ammonium Salts
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Cross-electrophile couplings between two electrophiles are powerful and economic methods to generate C-C bonds in the presence of stoichiometric external reductants. Herein, we report a novel strategy to realize the first external-reductant-free cross-electrophile coupling via visible-light photoredox catalysis. A variety of tetraalkyl ammonium salts, bearing primary, secondary, and tertiary C-N bonds, undergo selective couplings with aldehydes/ketone and CO2. Notably, the in situ generated byproduct, trimethylamine, is efficiently utilized as the electron donor. Moreover, this protocol exhibits mild reaction conditions, low catalyst loading, broad substrate scope, good functional group tolerance, and facile scalability. Mechanistic studies indicate that benzyl radicals and anions might be generated as the key intermediates via photocatalysis, providing a new direction for cross-electrophile couplings.
- Liao, Li-Li,Cao, Guang-Mei,Ye, Jian-Heng,Sun, Guo-Quan,Zhou, Wen-Jun,Gui, Yong-Yuan,Yan, Si-Shun,Shen, Guo,Yu, Da-Gang
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p. 17338 - 17342
(2019/01/04)
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- A General, Activator-Free Palladium-Catalyzed Synthesis of Arylacetic and Benzoic Acids from Formic Acid
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A new catalyst for the carboxylative synthesis of arylacetic and benzoic acids using formic acid (HCOOH) as the CO surrogate was developed. In an improvement over previous work, CO is generated in situ without the need for any additional activators. Key to success was the use of a specific system consisting of palladium acetate and 1,2-bis((tert-butyl(2-pyridinyl)phosphinyl)methyl)benzene. The generality of this method is demonstrated by the synthesis of more than 30 carboxylic acids, including non-steroidal anti-inflammatory drugs (NSAIDs), under mild conditions in good yields.
- Wang, Lin,Neumann, Helfried,Beller, Matthias
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supporting information
p. 6910 - 6914
(2018/06/04)
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- Regio- and Stereoselective Oxidation of Styrene Derivatives to Arylalkanoic Acids via One-Pot Cascade Biotransformations
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Green and selective oxidation methods are highly desired in chemical synthesis and manufacturing. In this work, we have developed a biocatalytic method for the regio- and stereoselective oxidation of styrene derivatives into arylacetic and (S)-2-arylpropionic acids via a one-pot epoxidation–isomerization–oxidation sequence. This was done via the engineering of Escherichia coli (StyABC-EcALDH) coexpressing styrene monooxygenase (SMO), styrene oxide isomerase (SOI) and aldehyde dehydrogenase (EcALDH) as an active and easily available whole-cell catalyst. Regioselective oxidation of styrene and 11 substituted styrenes using the E. coli cells was performed in a one-pot set-up, producing 12 phenylacetic acids in both high conversion and high yield. Engineering of E. coli (StyABC-ADH9v1) coexpressing SMO, SOI and ADH9v1 (a mutated alcohol dehydrogenase) led to biocatalysts capable of regio- and stereoselective oxidation of α-methylstyrene derivatives to the corresponding chiral acids. One-pot asymmetric synthesis of 4 (S)-2-arylpropionic acids was achieved in good conversion and excellent ee with the E. coli cells. This is a new type of asymmetric alkene oxidation to give chiral acids with no chemical counterpart thus far. The cascade bio-oxidation operates under mild conditions, uses molecular oxygen, exhibits very high regio- and enantioselectivity, and gives high conversion, thus providing a green and efficient method for the synthesis of arylacetic acids and (S)-2-arylpropionic acids directly from easily available styrenes. (Figure presented.).
- Wu, Shuke,Zhou, Yi,Seet, Daniel,Li, Zhi
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p. 2132 - 2141
(2017/06/23)
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- Palladium-Catalyzed Carboxylation of Benzyl Chlorides with Atmospheric Carbon Dioxide in Combination with Manganese/Magnesium Chloride
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An efficient direct carboxylation of a series of benzyl chlorides with CO2 catalyzed by Pd(OAc)2/dicyclohexyl (2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (SPhos) was developed to afford the corresponding phenylacetic acids in combination with Mn powder as a reducing reagent and MgCl2 as an indispensable additive. The reaction proceeded smoothly under 1 atm CO2. The application of Mn powder instead of a sensitive reducing reagent represents an operationally simple access to phenylacetic acids. Notably, MgCl2 is able to stabilize the (SPhos)2PdII(Bn)(Cl)(η1-CO2)(MgCl2) adduct and thus facilitates CO2 insertion into the PdII-C bond, which is supported by a DFT study. Specific effect: MgCl2 facilitates the direct insertion of CO2 into the PdII-C bond by stabilizing the PdII-CO2 adduct. With MgCl2 as an indispensable additive, the Pd-catalyzed carboxylation of various benzyl chlorides proceeded smoothly under 1 atm CO2, and the application of Mn powder instead of a sensitive reducing reagent makes this protocol an operationally simple access to phenylacetic acids.
- Zhang, Shuai,Chen, Wei-Qiang,Yu, Ao,He, Liang-Nian
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p. 3972 - 3977
(2016/01/26)
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- An efficient one pot method for synthesis of carboxylic acids from nitriles using recyclable ionic liquid [bmim]HSO4 Dedicated to my mentor Professor (Mrs.) Krishna Misra on her 76th birthday
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Environmentally benign ionic liquid [bmim]HSO4 was found suitable for conversion of nitriles into carboxylic acids under mild conditions with excellent purity.
- Kumar, Satyanand,Dixit, Sandeep Kumar,Awasthi, Satish Kumar
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supporting information
p. 3802 - 3804
(2014/07/07)
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- Palladium-catalyzed silver-mediated α-arylation of acetic acid: A new approach for the α-arylation of carbonyl compounds
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A new approach for the α-arylation of acetic acid through Pd-catalyzed silver-mediated direct C-H arylation of acetic acid with aryl iodides was developed. This protocol provided a straightforward method for the synthesis of a diverse set of α-phenylacetic acids. Palladium served on a silver platter: A new approach for the α-arylation of acetic acid through Pd-catalyzed silver-mediated direct C-H arylation of acetic acid with aryl iodides is presented. This protocol provides a straightforward method for the synthesis of a diverse set of α-phenylacetic acids. Deuteration experiments are performed to help elucidate the reaction mechanism.
- Wu, Guo-Jie,Guan, Jing,Han, Fu-She,Zhao, Yu-Long
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p. 1589 - 1593
(2014/06/24)
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- PROCESS FOR SYNTHESIZING PHENYLACETIC ACID BY CARBONYLATION OF TOLUENE
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A production process for substituted phenylacetic acids or ester analogues thereof is disclosed. In this process toluene or toluene substituted with various substituents, an alcohol, an oxidant and carbon monoxide are used as raw materials to obtain compounds comprising structure of phenylacetic acid ester or analogues thereof by catalysis of the complex catalyst formed from transition metal and ligand, and such compounds are hydrolyzed to obtain various substituted phenylacetic acid based compounds. This type of compounds and their derivatives serve as important fine chemicals used widely in the industries of pharmaceuticals, pesticides, perfume and the like.
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- An efficiently cobalt-catalyzed carbonylative approach to phenylacetic acid derivatives
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A highly efficient cobalt-catalyzed carbonylative approach to phenylacetic acid derivatives under one atmosphere pressure is reported. This methodology represents a useful extension of benzimidazole used as ligand in metal catalysis, and the catalytic mechanism has been proved by computer simulation. Notably, this new cobalt precatalyst, which promotes the carbonylation reaction dramatically and has already been used for scale-up experiment of phenylacetic acid derivatives.
- She, Meng-Yao,Xiao, Da-Wei,Yin, Bing,Yang, Zheng,Liu, Ping,Li, Jian-Li,Shi, Zhen
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p. 7264 - 7268
(2013/08/23)
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- Exalted resonance demands in the substituent effects on the acetolyses of 2-arylethyl trifluoromethanesulfonates destabilized by cn and cf3 groups
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Substituent effects on the acetolysis rates of 2-aryl-l-cyano-l- (trifluoromethyl)ethyl trifluoromethanesulfonates (α-OTf) and 2-aryl-2-cyano-2-(trifluoromethyl)ethyl trifluoromethanesulfonates (ss-OTf) were investigated by using LArSR equation. The obtained p and r+ values were p = -3.28, r+ = 0.98 and p = -3.48,r+ = 0.93 for the acetolysis of α-OTf and ss-OΥi, respectively. The obtained p values are comparable to those for typical aryl-assisted solvolyses, but the r+ values are much larger. The large r+ values suggest that the ester bond cleavages in the deactivated aryl-assisted solvolyses are assisted by the strong participation of the ss-aryl group.
- Usui, Satoshi,Tsuboya, Shoko,Umezawa, Yukthiro,Hazama, Ken,Okamura, Mutsuo
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experimental part
p. 254 - 260
(2009/05/30)
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- Negishi-type coupling of bromoarenes with dimethylzinc
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Treatment of bromoarenes with dimethylzinc in the presence of a palladium catalyst provides a high-yielding route to methylarenes. The process accommodates a wide range of aromatic substituents and, in the majority of cases, is free of side reactions.
- Herbert, John M.
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p. 817 - 819
(2007/10/03)
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- Quinolones as gonadotropin releasing hormone (GnRH) antagonists: Simultaneous optimization of the C(3)-aryl and C(6)-substituents
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A series of 3-arylquinolones was prepared and evaluated for their ability to act as gonadotropin releasing hormone (GnRH) antagonists. A variety of substitution patterns of the 3-aryl substituent are described. The 3,4,5-trimethylphenyl substituent (23h) was found to be optimal. (C) 2000 Elsevier Science Ltd. All rights reserved.
- Young, Jonathan R.,Huang, Song X.,Chen, Irene,Walsh, Thomas F.,DeVita, Robert J.,Wyvratt Jr., Matthew J.,Goulet, Mark T.,Ren, Ning,Lo, Jane,Yang, Yi Tien,Yudkovitz, Joel B.,Cheng, Kang,Smith, Roy G.
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p. 1723 - 1727
(2007/10/03)
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- Thermodynamic and nuclear magnetic resonance study of the reactions of α- and β-cyclodextrin with acids, aliphatic amines, and cyclic alcohols
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Titration calorimetry was used to determine equilibrium constants and standard molar enthalpy, Gibbs energy, and entropy changes for the reactions of a series of acids, amines, and cyclic alcohols with α- and β-cyclodextrin. The results have been examined in terms of structural features in the ligands such as the number of alkyl groups, the charge number, the presence of a double bond, branching, and the presence of methyl and methoxy groups. The values of thermodynamic quantities, in particular the standard molar Gibbs energy, correlate well with the structural features in the ligands. These structural correlations can be used for the estimation of thermodynamic quantities for related reactions. Enthalpy-entropy compensation is evident when the individual classes of substances studied herein are considered, but does not hold when these various classes of ligands are considered collectively. The NMR results indicate that the mode of accommodation of the acids and amines in the α-cyclodextrin cavity is very similar, but that the 1-methyl groups in 1-methylhexylamine and in 1-methylheptylamine and the N-methyl group in N-methylhexylamine lie outside the α-cyclodextrin cavity. This latter finding is consistent with the calorimetric results. Many of the thermodynamic and NMR results can be qualitatively understood in terms of van der Waals forces and hydrophobic effects.
- Rekharsky, Mikhail V.,Mayhew, Martin P.,Goldberg, Robert N.,Ross, Philip D.,Yamashoji, Yuko,Inoue, Yoshihisa
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- Catalytic carbonylation of benzylic and allylic bromides by a rhodium zwitterionic complex under phase transfer catalysis conditions
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The zwitterionic rhodium complex, (COD)Rh(η6-C6H5BPh3) (1), can catalyze the carbonylation of benzylic and allylic bromides in the presence of 5 N NaOH and CH2Cl2 at atmospheric pressure and 40 deg C, with (C6H13)4N+ HSO4- as the phase transfer catalyst, to give carboxylic esters as the major products. Keywords: Rhodium; Carbonylation; Zwitterionic complex; Phase transfer catalysis
- Amaratunga, Shiyamalie,Alper, Howard
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- Photolysis of the 1-naphthylmethyl ester of substituted phenylacetic acids: intramolecular charge transfer and rates of decarboxylation of arylacyl radicals
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The photolysis of esters 6 and 8 in methanol leads to products resulting from both naphthylmethyl cations and radicals.The product distribution is nearly independent of X for the esters 6 except when X equals methoxy.A mechanism involving initial homolytic cleavage of the carbon-oxygen bond in the excited singlet state of the ester is proposed.Competition between electron transfer in the radical pair to form the ion pair and decarboxylation of the arylacyloxy radical allows calculations of the rates of this decarboxylation process.The ρ values versus ? is close to zero.When X equals methoxy, intramolecular electron transfer occurs with the naphthalene ring serving as the acceptor and the methoxyaromatic as the donor.This exciplex fragments to carbon dioxide and 1-(1-naphthyl)-2-arylethane. Key words: acyloxy radical, decarboxylation, photolysis of benzylic esters.
- Hilborn, James W.,Pincock, James A.
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p. 992 - 999
(2007/10/02)
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- Facile Cleavage of Bibenzyls by Cs-K-Na Alloy Leading to the Formation of Benzyl Carbanions
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Facile cleavage of twelve substituted bibenzyls (1-12) with Cs-K-Na alloy at -75 deg C leading to the formation of benzyl carbanions has been studied.
- Sengupta, Dibyendu,Grovenstein, E.
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p. 185 - 186
(2007/10/02)
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- THE DIPHENYLMAFNESIUM/ALKALI METAL ALKOXIDE SYSTEM. HYDROCARBON-SOLUBLE ORGANOALKALI METAL REAGENTS
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Unsolvated diphenylmagnesium is solubilized in aromatic hydrocarbon solvents by an alkali metal 2-ethoxyethoxide.The mode of interaction between Ph2Mg and MOCH2CH2OEt (M=Li, Na, K) varies with M.For M=Li the complex formed has an Mg/Li ratio equal to 1.3/1.0, and is evidently different from the PhLi/Mg(OCH2CH2OEt) complex.For M=Na the metal-metal interchange apparently leads to a complex identical to thaht derived from PhNa and Mg(OCH2CH2OEt).For M=K the results are not conclusive.The width of the resonance 13C from the ipso-carbon, increases with increasing ionic radius, and for M=K the signal is too broad to be clearly observed .The ipso-carbon in the NMR spectrum of the PhNa/Mg(OCH2CH2OEt) complex has now been shown to give rise to resonance at 175.95 ppm.Metalation experiments involving Ph2Mg along with two equivalents of MOCH2CH2OEt indicated that reactivity increases in the order Li Na K.
- Screttas, Constantinos G.,Micha-Screttas, Maria
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- Ru(III) Catalysed Oxidation of Aryl Styryl Ketones by Periodate in Acid Medium: A Kinetic Study
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Oxidation of unsubstituted and substituted phenyl styryl ketones by periodate in the presence of Ru(III) is first order each in and and fractional order in .The rate of reaction increases with decrease in .Each mol of aryl styryl ketone consumes two mol of periodate for complete oxidation and the products have been identified as the corresponding substituted benzoic acids and phenylacetic acids.A probable mechanism involves the formation of a 1:1 complex between Ru(III) and the substrate which is oxidised by periodate to Ru(V) complex in rate-determining step which later dissociates to give products.
- Swarnalakshmi, N.,Uma, V.,Sethuram, B.,Navaneeth Rao, T.
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p. 386 - 388
(2007/10/02)
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- Carbanions. 23. Cleavage of 1,2-Diphenylethane and Derivatives by Cs-K-Na Alloy. Cometitive Rates of Bond Scission
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The following hydrocarbons are cleaved at a C-C bond to allylic and or/benzylic cesium compounds within 2 h by Cs-K-Na alloy in THF at -75 deg C: meso-2,3-diphenylbutane, 2,3-dimethyl-2,3-diphenylbutane, 1,2,2-triphenylpropane, 4-phenyl-1-butene, bibenzyl, and eight o-,m-, or p-methyl derivatives of bibenzyl.Under the same conditions 2-methyl- and 3-methyl-4-phenyl-1-butene were partially cleaved, 4,4'-dimethylbibenzyl was only slightly cleaved, and 9,10-dihydrophenanthrene was not detectably cleaved, while 10,11-dihydro-5H-dibenzocycloheptene underwent alternative C-H bond cleavage.Under the present reaction conditions 4,4'-dimethylbibenzyl and 9,10-dihydrophenanthrene were converted largely to dianions.It is suggested that all of the compounds undergoing cleavage are converted to dianions prior to cleavage.From competitive experiments the rates of reductive cleavage of most of these hydrocarbons relative to bibenzyl have been measured at -75 deg C.The relative rates of cleavage of m- and p-methylderivatives of bibenzyl may be correlated with the relative equilibrium acidities of toluene, m-xylene, and p-xylene in a modified Hammett relationship.Cleavages of benzylic C-C bonds are believed to occur by way of a preferred transition-state geometry,7, which permits the ?* orbital of the bond undergoing cleavage to interact with the HOMO's of both aromatic rings.Compounds that cannot attain this transition-state geometry are cleaved slowly if at all.The variable effect upon reaction rate of methyl groups near the bond undergoing cleavage are discussed in terms of ground-state and transition-state atrain, solvation, and polarizability of methyl groups.According to labeling experiments (o-methylbenzyl)cesium undergoes ready intramolecular sigmatropic migration of hydrogen from the methyl group to the methylene group when warmed from -75 deg C to near room temperature.
- Grovenstein, Erling,Bhatti, Amjad M.,Quest, Dean E.,Sengupta, Dibyendu,VanDerveer, Don
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p. 6290 - 6299
(2007/10/02)
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- CATALYTIC PHASE TRANSFER CARBONYLATION OF BENZYL HALIDES WITH IRON PENTACARBONYL.
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Benzyl halides are readily carbonylated to arylacetic acids in a two-phase system (aqueous sodium hydroxide (1M), tetrabutylammonium sulfate ; organic phase (CH2Cl2 or C6H6 or C6H5CH3)), using a catalytic amount of the cheap, easy to handle iron pentacarbonyl under carbon monoxide atmosphere.
- Tanguy, Guy,Weinberger, Berndt,Abbayes, Herve des
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p. 4005 - 4008
(2007/10/02)
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