5848-56-6Relevant academic research and scientific papers
Catalytic reductive deoxygenation of esters to ethers driven by hydrosilane activation through non-covalent interactions with a fluorinated borate salt
Agbossou-Niedercorn, Francine,Dixit, Ruchi,Merle, Nicolas,Michon, Christophe,Rysak, Vincent,Trivelli, Xavier,Vanka, Kumar
, p. 4586 - 4592 (2020/08/14)
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.
Remarkably high catalyst efficiency of a disilaruthenacyclic complex for hydrosilane reduction of carbonyl compounds
Tahara, Atsushi,Sunada, Yusuke,Takeshita, Takashi,Inoue, Ryoko,Nagashima, Hideo
supporting information, p. 11192 - 11195 (2018/10/24)
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.
A Versatile Iridium(III) Metallacycle Catalyst for the Effective Hydrosilylation of Carbonyl and Carboxylic Acid Derivatives
Corre, Yann,Rysak, Vincent,Trivelli, Xavier,Agbossou-Niedercorn, Francine,Michon, Christophe
supporting information, p. 4820 - 4826 (2017/09/07)
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.
SNAAP sulfonimidate alkylating agent for acids, alcohols, and phenols 1
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
, p. 3361 - 3368 (2014/01/06)
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.
Synthesis of ethers from esters via Fe-catalyzed hydrosilylation
Das, Shoubhik,Li, Yuehui,Junge, Kathrin,Beller, Matthias
supporting information, p. 10742 - 10744 (2013/01/15)
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.
Reduction of esters to ethers utilizing the powerful lewis acid BF 2OTf·OEt2
Morra, Nicholas A.,Pagenkopf, Brian L.
, p. 511 - 514 (2008/12/21)
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
Direct reduction of esters to ethers with an indium(III) bromide/triethylsilane catalytic system
Sakai, Norio,Moriya, Toshimitsu,Fujii, Kohji,Konakahara, Takeo
experimental part, p. 3533 - 3536 (2009/05/07)
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.
Efficient H/D exchange reactions of alkyl-substituted benzene derivatives by means of the Pd/C-H2-D2O system
Esaki, Hiroyoshi,Aoki, Fumiyo,Umemura, Miho,Kato, Masatsugu,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
, p. 4052 - 4063 (2008/02/08)
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.
An efficient one-pot synthesis of unsymmetrical ethers: A directly reductive deoxygenation of esters using an InBr3/Et3SiH catalytic system
Sakai, Norio,Moriya, Toshimitsu,Konakahara, Takeo
, p. 5920 - 5922 (2008/02/09)
(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.
A triruthenium carbonyl cluster bearing a bridging acenaphthylene ligand: An efficient catalyst for reduction of esters, carboxylic acids, and amides by trialkylsilanes
Matsubara, Kouki,Iura, Takafumi,Maki, Tomoyuki,Nagashima, Hideo
, p. 4985 - 4988 (2007/10/03)
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.
