- Molybdenum (VI)-catalyzed dehydrative construction of C[sbnd]O and C[sbnd]S bonds formation via etherification and thioetherification of alcohols and thiols
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An inexpensive, easily available, environmentally benign, and efficient catalyst molybdenum(VI) dioxo (acetylacetonate)2 was used for the direct oxo- and thioetherification of alcohol. This method endures selective molybdenum catalyzed dehydrative synthesis of symmetrical ethers from benzylic secondary alcohols as well as unsymmetrical ethers from the reaction of benzylic secondary alcohols with primary alcohol. Furthermore, we have been also successful in the synthesis of Aryl thioether by using alcohol and thiols.
- Singh, Rahulkumar Rajmani,Srivastava, Radhey S.,Whittington, Alex
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- W-Ti-O mixed metal oxide catalyzed dehydrative cross-etherification of alcohols
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A dehydrative cross-etherification reaction of two different alcohols is achieved in the presence of hydrothermally synthesized tungsten-titanium mixed metal oxide (W-Ti-O) catalyst. The reaction is environmentally benign: organic solvent is not necessary and the catalyst is readily recovered and reusable.
- Yada, Akira,Murayama, Toru,Hirata, Jun,Nakashima, Takuya,Tamura, Masanori,Kon, Yoshihiro,Ueda, Wataru
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p. 447 - 449
(2018/03/27)
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- Direct and efficient synthesis of unsymmetrical ethers from alcohols catalyzed by Fe(HSO4)3 under solvent-free conditions
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Highly efficient Fe(HSO4)3 catalyzed etherification of primary, secondary and tertiary benzylic alcohols with primary and secondary aliphatic alcohols is reported. The reaction affords unsymmetrical benzyl ethers in good to excellent yields under solvent-free conditions.
- Moghadam, Bashir Nazari,Akhlaghinia, Batool,Rezazadeh, Soodabeh
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p. 1487 - 1501
(2016/04/26)
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- Sulfated tungstate as hydroxyl group activator for preparation of benzyl, including p-methoxybenzyl ethers of alcohols and phenols
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Sulfated tungstate was found to be an effective heterogeneous and reusable catalyst for hydroxy group activation–mediated preparation of benzylic ethers including p-methoxybenzylic ethers of a wide range of alcohols and phenols under mild reaction conditions.
- Katkar, Kamlesh V.,Veer, Sachin D.,Akamanchi, Krishnacharya G.
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supporting information
p. 1893 - 1901
(2016/11/25)
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- Novel gallium and indium salts of the 12-tungstophosphoric acid: Synthesis, characterization and catalytic properties
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The objective of this study was the preparation, characterization and testing of the catalytic properties of the GaPW12O40 and InPW12O40 salts of 12-tungstophosphoric heteropolyacid (HPW). The samples were characterized by XRD, IR, SEM, and 31P and 1H MAS NMR spectroscopy. The acid properties of the solids were directly accounted for by applying 1H MAS NMR. The salts were screened in the etherification of 1-phenylethanol with C1-C 4 alkanols in dichloromethane as a solvent to yield the corresponding C6H5CH(OR)CH3 unsymmetrical ethers. In comparison with pure HPW, the new salts revealed generally a higher selectivity of ethers formation at 65 °C.
- Filek, Urszula,Mucha, Dariusz,Hunger, Michael,Sulikowski, Bogdan
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- Direct synthesis of unsymmetrical ethers from alcohols catalyzed by titanium cation-exchanged montmorillonite
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Titanium-exchanged montmorillonite (Ti4+-mont) was found to act as an efficient heterogeneous catalyst for the etherification of a wide range of alcohols under mild reaction conditions. Ti4+-mont was reusable with retention of high efficiency and applicable to scale-up reaction conditions. The Royal Society of Chemistry 2012.
- Mitsudome, Takato,Matsuno, Tsuyoshi,Sueoka, Shoichiro,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
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supporting information; experimental part
p. 610 - 613
(2012/04/23)
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- Oxidative nucleophilic substitution: Transformation of alkylboronic derivatives
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An efficient amidation reaction is described in this paper. Potassium alkyltrifluoroborate salts can be transforming to amides from nitriles in the presence of copper acetate and boron trifluoride. An extension of this reaction allowed the formation of amines, ethers, and C-C bond.
- Cazorla, Clément,Métay, Estelle,Lemaire, Marc
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experimental part
p. 8615 - 8621
(2011/11/30)
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- Palladium-catalyzed inter- and intramolecular hydroamination of styrenes coupled with alcohol oxidation using N-fluorobenzenesulfonimide as the oxidant
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Palladium-catalyzed inter- and intramolecular hydroaminations of styrenes that are coupled to alcohol oxidation under oxidative condition are reported. The fluorination reagent NFSI is used as the nitrogen source as well as the oxidant. Bidental nitrogen
- Xu, Tao,Qiu, Shuifa,Liu, Guosheng
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experimental part
p. 46 - 49
(2011/02/17)
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- Silica-supported KHSO4: An efficient system for activation of aromatic terminal olefins
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Potassium hydrogen sulfate adsorbed on chromatography-grade silica gel activates electron-rich aromatic terminal olefins towards nucleophilic attack at the benzylic position by alcohols. Temperature plays a crucial role and facilitates suppressing nucleophilic reaction in favor of dimerization of the terminal olefin. Georg Thieme Verlag Stuttgart - New York.
- Das, Ram Nath,Sarma, Kuladip,Pathak, Madan Gopal,Goswami, Amrit
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supporting information; experimental part
p. 2908 - 2912
(2011/02/25)
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- Effective Au(III)-CuCl2-catalyzed addition of alcohols to alkenes
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Alkenes can be activated by Au(III) catalysts, and the effective addition of alcohols to alkenes can be carried out under mild conditions with Au(III), provided that catalytic amounts of CuCl2 are added, which significantly stabilize the cationic Au(III). The Royal Society of Chemistry.
- Zhang, Xin,Corma, Avelino
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p. 3080 - 3082
(2008/02/10)
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- Efficient and selective formation of mixed acetals by Nafion-H SAC-13 silica nanocomposite solid acid catalyst
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Various types of hydroxy compounds can readily be converted to the corresponding mixed acetals with dialkoxymethanes in the presence of SAC-13 solid superacid. The transformation is almost instantaneous, product acetals are isolated in good to excellent yields, and the catalyst can be reused with minor loss of activity. Comparative studies were also carried out with p-toluenesulfonic acid and BF3·OEt2.
- Ledneczki, Istvan,Molnar, Arpad
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p. 3683 - 3690
(2007/10/03)
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- Lewis acid-catalyzed reductive etherification of carbonyl compounds with alkoxyhydrosilanes
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The TMSI-catalyzed reaction of aldehydes and ketones with alkoxydimethylsilanes gave unsymmetrical ethers in good to high yields. This reductive etherification is superior to the conventional method using two kinds of silicon reagents in terms of atom eff
- Miura, Katsukiyo,Ootsuka, Kazunori,Suda, Shuntaro,Nishikori, Hisashi,Hosomi, Akira
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p. 313 - 315
(2007/10/03)
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- BiBr3, an efficient catalyst for the benzylation of alcohols: 2-Phenyl- 2-propyl, a new benzyl-type protecting group
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The benzylation of aliphatic alcohols with various benzylic alcohols has been achieved in the presence of BiBr3 under mild conditions. 2- Phenylpropan-2-ol proved to be the most efficient and can be considered as a novel protecting group. (C) 2000 Elsevier Science Ltd.
- Boyer, Bernard,Keramane, El-Mehdi,Roque, Jean-Pierre,Pavia, André A.
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p. 2891 - 2894
(2007/10/03)
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- Use of Polyoxetane Resin-Supported Quaternary Onium Salts as a Polymeric Phase-Transfer Catalyst for Preparing Ethers from Hydroxy Compounds and Alkyl Halides
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As a polymer support for preparing polymeric phase-transfer catalysts (PTC), soft, moderately polar polyoxetane resins were employed which were synthesized by a cationic ring-opening copolymerization of oxetanes Br(CH2)nOCH2-X with bisoxetanes X-CH2O(CH2)nOCH2-X, where X=3-methyl-3-oxetanyl and n=4 or 6.In a few cases of those polymerizations, 3-(2-oxadecyl)-3-methyloxetane was used as a comonomer with a lipophilic pendant.The terminal bromine of the pendant groups of such polyoxetane resins was quaternized with tributylamine or tributylphosphine in DMF in order to examine the phase-transfer catalyzing ability of the resultant quaternary onium bromides in the etherification reaction between alkyl halides and alcohols or phenols.These reactions gave the desired products in fairly good yields within reaction periods of 1-3 h, indicating that the catalytic activities of those PTCs are comparable to that of tetrabutylammonium bromide.A fairly high catalytic activity of the polymeric PTC was observed at each of ten stages in a process using the polymeric PTC repeatedly for the etherification reaction of 3-hydroxymethyl-3-methyloxethane with 1,4-dibromobutane.
- Motoi, Masatoshi,Shimamura, Katsuhiko,Shimamura, Chikako,Muramoto, Satoru,Kanoh, Shigeyoshi,Suda, Hiroshi
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p. 2553 - 2561
(2007/10/02)
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- ENHANCED NUCLEOPHILE SELECTIVITY IN THE PHOTOADDITION TO STYRENE. COMPARISON WITH THE THERMAL ADDITION
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The reactivity-selectivity properties of the sec-phenethyl carbenium ion and its analogues have been examined in binary-aqueous solutions of alcohols (ROH; R = Me, Et, CF3CH2, n-Bu, t-Bu, n-Pr, i-Pr), acetic acid, and in solutions containig external nucleophiles such as thiophenol, ethanethiol, acetate, and benzenesulfinate.Selectivity (S = k(Nuc)/k(H2O) is observed to be a function of the nucleophile, the ring substituent, thermal or photochemical conditions, irradiation time, and medium acidity.In the case of styrene, the photochemically generated (usually 254 nm, 1 h) species exhibits greater selectivity (up to two orders of magnitude) than its thermal counterpart, generated (usually 80 deg C, 2-4 d) in identical media, particularly in aqueous-rich solvent compositions.A rationale for these differences, supported by fluorescence quenching experiments, and the other effects upon selectivity will be discussed.
- Anderson, Steven W.,Yates, Keith
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p. 2412 - 2421
(2007/10/02)
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