496-14-0Relevant academic research and scientific papers
A green process for the oxidative lactonization of 1,2-benzenedimethanol by tungstic acid with aqueous H2O2
Zhu, Quan-Jing,Dai, Wei-Lin,Fan, Kang-Nian
, p. 205 - 208 (2010)
A new economic and green route to synthesize phthalide from 1,2-benzenedimethanol using aqueous hydrogen peroxide as the oxidant and tungstic acid as the catalyst under organic solvent-free conditions is presented. This process proceeds with advantages from the viewpoint of green chemistry, in which the only by-product of H2O2 is water and the catalyst can also be easily recovered. The desired product with high purity and good yield can be conveniently obtained when cooled after reaction.
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.
One-Pot Synthesis of O-Heterocycles or Aryl Ketones Using an InCl3/Et3SiH System by Switching the Solvent
Jia, Wenqiang,Xi, Qiumu,Liu, Tianqi,Yang, Minjian,Chen, Yonghui,Yin, Dali,Wang, Xiaojian
, p. 5141 - 5149 (2019/05/10)
An efficient one-pot synthesis of O-heterocycles or aryl ketones has been achieved using Et3SiH in the presence of InCl3 via a sequential ionic hydrogenation reaction by switching the solvent. This methodology can be used to construct C-O bonds and to prepare conjugate reduction products, including chromans, tetrahydrofurans, tetrahydropyrans, dihydroisobenzofurans, dihydrochalcones, and 1,4-diones in a facile manner. In addition, a novel plausible mechanism involving a conjugate reduction and a tandem reductive cyclization was verified by experimental investigations.
An ether compound of green high-efficient synthetic method (by machine translation)
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Paragraph 0051, (2018/07/07)
The invention discloses an ether compound of green high-efficient synthetic method, energy-saving environmental protection, comprising: mild reaction system, uses aldehyde, silane as the starting material, under the action of the silver salt in a price, for in solvent-free conditions, through reducing the - coupling - cheng mi reaction, realization of high efficiency alcohol of preparation. Synthesis method of the invention has the advantages of low dosage of catalyst, solvent-free, conversion and high yield, the reaction time is short, safe and stable, easy to operate, the product only distillation purification without any additional organic solvent, the whole range of green, environmental protection, high efficiency and the like, can overcome the defects of the prior art, it has very good industrial application value. (by machine translation)
Cyclic ether synthesis from diols using trimethyl phosphate
Asai, Shota,Kato, Maho,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 4787 - 4790 (2017/07/06)
Cyclic ethers have been effectively synthesized via the intramolecular cyclization of diols using trimethyl phosphate and NaH. The present cyclization could proceed at room temperature to produce 5-7 membered cyclic ethers in good to excellent yields. Substrates possessing a chiral secondary hydroxy group were transformed into the corresponding chiral cyclic ethers along with the retention of their stereochemistries.
Lewis acid promoted ruthenium(II)-catalyzed etherifications by selective hydrogenation of carboxylic acids/esters
Li, Yuehui,Topf, Christoph,Cui, Xinjiang,Junge, Kathrin,Beller, Matthias
supporting information, p. 5196 - 5200 (2015/04/27)
Ethers are of fundamental importance in organic chemistry and they are an integral part of valuable flavors, fragrances, and numerous bioactive compounds. In general, the reduction of esters constitutes the most straightforward preparation of ethers. Unfortunately, this transformation requires large amounts of metal hydrides. Presented herein is a bifunctional catalyst system, consisting of Ru/phosphine complex and aluminum triflate, which allows selective synthesis of ethers by hydrogenation of esters or carboxylic acids. Different lactones were reduced in good yields to the desired products. Even challenging aromatic and aliphatic esters were reduced to the desired products. Notably, the in situ formed catalyst can be reused several times without any significant loss of activity. An assist from Al: A bifunctional catalyst system consisting of a Ru/phosphine complex and aluminum triflate allows selective hydrogenation of esters to ethers. A variety of lactones were reduced to the desired products in good yields. The catalyst further provides a general method for the reduction of linear esters and reductive etherification of carboxylic acids with alcohols.
Synthesis of five- and six-membered heterocycles by dimethyl carbonate with catalytic amounts of nitrogen bicyclic bases
Aricò,Evaristo,Tundo
, p. A1176 - A1185 (2015/03/04)
A catalytic amount of a nitrogen bicyclic base, i.e., DABCO, DBU or TBD, is effective for the one-pot synthesis of heterocycles from 1,4-, 1,5-diols and 1,4-bifunctional compounds via dimethyl carbonate chemistry under neat conditions. Nitrogen bicyclic bases that were previously shown to have enhanced the reactivity of DMC in methoxycarbonylation reaction by a BAc2 mechanism are herein used for the first time as efficient catalysts for cyclization reactions encompassing both BAc2 and BAl2 pathways. This synthesis procedure was also applied to a large scale synthesis of cyclic sugars, isosorbide and isomannide, starting from d-sorbitol and d-mannitol, respectively. The resulting anhydro sugar alcohols were obtained as pure crystalline compounds that did not require any further purification or crystallization. This journal is
Selective catalytic synthesis of unsymmetrical ethers from the dehydrative etherification of two different alcohols
Kim, Junghwa,Lee, Dong-Hwan,Kalutharage, Nishantha,Yi, Chae S.
, p. 3881 - 3885 (2015/01/16)
The cationic ruthenium-hydride complex [(C6H6)(PCy3)(CO)RuH]+BF4- catalyzes selective etherification of two different alcohols to form unsymmetrically substituted ethers. The catalytic method exhibits a broad substrate scope while tolerating a range of heteroatom functional groups in forming unsymmetrical ethers, and it is successfully used to directly synthesize a number of highly functionalized chiral nonracemic ethers.
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.
Synthesis of five-membered cyclic ethers by reaction of 1,4-diols with dimethyl carbonate
Aricó, Fabio,Tundo, Pietro,Maranzana, Andrea,Tonachini, Glauco
experimental part, p. 1578 - 1586 (2012/10/07)
The reaction of 1,4-diols with dimethyl carbonate in the presence of a base led to selective and high-yielding syntheses of related five-membered cyclic ethers. This synthetic pathway has the potential for a wide range of applications. Distinctive cyclic ethers and industrially relevant compounds were synthesized in quantitative yield. The reaction mechanism for the cyclization was investigated. Notably, the chirality of the starting material was maintained. DFT calculations indicated that the formation of five-membered cyclic ethers was energetically the most favorable pathway. Typically, the selectivity exhibited by these systems could be rationalized on the basis of hard-soft acid-base theory. Such principles were applicable as far as computed energy barriers were concerned, but in practice cyclization reactions were shown to be entropically driven. Copyright
