- Catalytic reductive deoxygenation of esters to ethers driven by hydrosilane activation through non-covalent interactions with a fluorinated borate salt
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We report the catalytic and transition metal-free reductive deoxygenation of esters to ethers through the use of a hydrosilane and a fluorinated borate BArF salt as a catalyst. Experimental and theoretical studies support the role of noncovalent interactions between the fluorinated catalyst, the hydrosilane and the ester substrate in the reaction mechanism.
- Agbossou-Niedercorn, Francine,Dixit, Ruchi,Merle, Nicolas,Michon, Christophe,Rysak, Vincent,Trivelli, Xavier,Vanka, Kumar
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p. 4586 - 4592
(2020/08/14)
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- Remarkably high catalyst efficiency of a disilaruthenacyclic complex for hydrosilane reduction of carbonyl compounds
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A disilaruthenacyclic complex (1) showed extremely high catalytic activity for hydrosilane reduction of aldehydes and ketones to silyl ethers and secondary and tertiary amides to the corresponding amines. An σ-CAM mechanism was proposed to explain the activity.
- Tahara, Atsushi,Sunada, Yusuke,Takeshita, Takashi,Inoue, Ryoko,Nagashima, Hideo
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supporting information
p. 11192 - 11195
(2018/10/24)
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- A Versatile Iridium(III) Metallacycle Catalyst for the Effective Hydrosilylation of Carbonyl and Carboxylic Acid Derivatives
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A versatile iridium(III) metallacycle catalysed rapidly and selectively the reduction of a large array of challenging esters and carboxylic acids as well as various ketones and aldehydes. The reactions proceeded in high yields at room temperature by hydrosilylation followed by desilylation. Although the reactions of various aldehydes and ketones resulted exclusively in alcohols, the hydrosilylation of esters led to alcohols or ethers, depending on the type of substrate. Regarding the carboxylic acids, again the nature of the reagent controlled the outcome of the hydrosilylation reaction, either alcohols or aldehydes being formed.
- Corre, Yann,Rysak, Vincent,Trivelli, Xavier,Agbossou-Niedercorn, Francine,Michon, Christophe
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supporting information
p. 4820 - 4826
(2017/09/07)
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- SNAAP sulfonimidate alkylating agent for acids, alcohols, and phenols 1
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Stable, crystalline ethyl N-tert-butyl-4-nitrobenzenesulfonimidate has been prepared in high yield by direct O-ethylation of N-tert-butyl-4- nitrobenzenesulfonamide with iodoethane and silver(I) oxide in dichloromethane. This sulfonimidate directly ethylates various acids to esters; the stronger the acid, the faster it alkylates and in higher yield. It readily ethylates alcohols and phenols to ethers at room temperature in the presence of tetrafluoroboric acid catalyst without molecular rearrangements or racemization. We have defined these reactions as SNAAP alkylations: [substitution, nucleophilic of acids, alcohols and phenols]. The hard sulfonimidate alkylating agent is chemoselective, preferring oxygen > nitrogen > sulfur. The sulfonamide byproduct of alkylation is readily recycled to the sulfonimidate. Georg Thieme Verlag Stuttgart . New York.
- Maricich, Tom J.,Allan, Matthew J.,Kislin, Brett S.,Chen, Andrea I-T.,Meng, Fan-Chun,Bradford, Christine,Kuan, Nai-Chia,Wood, Jeremy,Aisagbonhi, Omonigho,Poste, Alethea,Wride, Dustin,Kim, Sylvia,Santos, Therese,Fimbres, Michael,Choi, Dianne,Elia, Haydi,Kaladjian, Joseph,Abou-Zahr, Ali,Mejia, Arturo
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p. 3361 - 3368
(2014/01/06)
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- Synthesis of ethers from esters via Fe-catalyzed hydrosilylation
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Triiron dodecacarbonyl allows for the selective reduction of esters into the corresponding ethers. This protocol has a wide substrate scope. In addition, cholesteryl pelarogonate has been reduced under the reaction conditions with an excellent yield.
- Das, Shoubhik,Li, Yuehui,Junge, Kathrin,Beller, Matthias
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supporting information
p. 10742 - 10744
(2013/01/15)
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- Direct reduction of esters to ethers with an indium(III) bromide/triethylsilane catalytic system
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An indium(III) bromide-triethylsilane reagent system promotes direct reduction of esters to produce the corresponding unsymmetrical ethers. This simple catalytic system accommodated other carbonyl compounds, such as a tertiary amide and a carboxylic acid. Georg Thieme Verlag Stuttgart.
- Sakai, Norio,Moriya, Toshimitsu,Fujii, Kohji,Konakahara, Takeo
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experimental part
p. 3533 - 3536
(2009/05/07)
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- Reduction of esters to ethers utilizing the powerful lewis acid BF 2OTf·OEt2
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The direct reduction of esters to their corresponding ethers has been achieved using the Lewis acid BF2OTf·OEt2 generated via anionic redistribution between TMSOTf and BF3·OEt 2 with triethylsilane acting as the
- Morra, Nicholas A.,Pagenkopf, Brian L.
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p. 511 - 514
(2008/12/21)
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- An efficient one-pot synthesis of unsymmetrical ethers: A directly reductive deoxygenation of esters using an InBr3/Et3SiH catalytic system
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(Chemical Equation Presented) This study describes a novel one-pot procedure for a directly reductive conversion of the carbonyl function of esters to the corresponding ethers by Et3SiH in the presence of a catalytic amount of InBr3.
- Sakai, Norio,Moriya, Toshimitsu,Konakahara, Takeo
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p. 5920 - 5922
(2008/02/09)
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- Efficient H/D exchange reactions of alkyl-substituted benzene derivatives by means of the Pd/C-H2-D2O system
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A method for efficient and extensive H/D exchange of substituted benzene derivatives which is catalyzed by heterogeneous Pd/C in D2O as a deuterium source under hydrogen atmosphere is described. Multideuterium incorporation into unactivated linear or branched alkyl chains that bear a carboxyl, hydroxyl, ether, ester, or amide moiety and are connected with a benzene ring was achieved by using the Pd/C-H2-D2O system. The present method does not require expensive deuterium gas or any special equipment.
- Esaki, Hiroyoshi,Aoki, Fumiyo,Umemura, Miho,Kato, Masatsugu,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
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p. 4052 - 4063
(2008/02/08)
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- A triruthenium carbonyl cluster bearing a bridging acenaphthylene ligand: An efficient catalyst for reduction of esters, carboxylic acids, and amides by trialkylsilanes
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An efficient reduction of carboxylic acids, esters, and amides with trialkylsilanes is accomplished using a triruthenium carbonyl cluster bearing a bridging acenaphthylene ligand, (μ3,η2:η3:η5 -acenaphthylene)Ru3(CO)7, as the catalyst. Preactivation of the catalyst by hydrosilanes accelerates the reactions. Sterically small trialkylsilanes are effective in these reactions. Reduction of carboxylic acids and amides efficiently produces the corresponding silyl ethers and amines, respectively. Reduction of esters gives a mixture of silyl and alkyl ethers, but can be controlled by changing the silanes and solvents.
- Matsubara, Kouki,Iura, Takafumi,Maki, Tomoyuki,Nagashima, Hideo
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p. 4985 - 4988
(2007/10/03)
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- Synthesis and Physical Properties of Alkoxymethylene Substituted Phenyl Cyclohexanecarboxylates
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The homologous series of 4-alkoxymethylene-substituted-phenyl 4'-alkylcyclohexanecarboxylates are prepared.And their transition temperatures, bulk viscosities and birefringences have been measured comparing with the series of 4-alkoxy-substituted-phenyl 4'-alkylcyclohexanecarboxylates.The differences between the alkoxymethylene-substituted series and alkoxy-substituted series are discussed.Alkoxymethylene groups contribute to lowering the transition temperatures, and also reducing the bulk viscosities and optical anisotropy compared to the alkoxy groups as terminal groups of mesogens.This is apparently due to the higher flexibility of the alkoxymethylene groups, which affected the packing of molecules.
- Kitamura, Teruo,Mukoh, Akio,Era, Susumu,Fujii, Tsunenori
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p. 231 - 248
(2007/10/02)
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- Carbene in Rigid Matrix. XI. Temperature and Matrix Effect on Phenylcarbene Processes in Ether and Amine
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Product distributions from reactions of phenylcarbene with diethyl or diisopropyl ether or diethylamine were found to be highly dependent on reaction temperature.As temperature decreases, the C-O displacement reaction and N-H insertion are decreased.Concomitantly, primary C-H insertion products markedly increase especially at lower matrix temperatures.
- Tomioka, Hideo,Suzuki, Shinji,Izawa, Yasuji
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p. 492 - 495
(2007/10/02)
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- PHOTOINDUCED OXIDATIVE CLEAVAGE OF ARYLCYCLOPROPANES IN THE PRESENCE OF ORGANIC ELECTRON-ACCEPTOR
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The cyclopropane ring of arylcyclopropanes is oxidatively cleaved by irradiation in polar solvents containing nucleophiles such as alcohols, water, and sodium cyanide in the presence of electron-acceptor such as 1,4-dicyanobenzene and 1-cyanonaphthalene, giving nucleophile-incorporated products.This photoreaction proceeds via an electron-transfer from the cyclopropanes to the excited electron-acceptors, and the cation radicals of arylcyclopropanes are involved as key intermediates.
- Mizuno, Kazuhiko,Ogawa, Jun,Otsuji, Yoshio
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p. 741 - 744
(2007/10/02)
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