- Dehydrogenative ester synthesis from enol ethers and water with a ruthenium complex catalyzing two reactions in synergy
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We report the dehydrogenative synthesis of esters from enol ethers using water as the formal oxidant, catalyzed by a newly developed ruthenium acridine-based PNP(Ph)-type complex. Mechanistic experiments and density functional theory (DFT) studies suggest that an inner-sphere stepwise coupled reaction pathway is operational instead of a more intuitive outer-sphere tandem hydration-dehydrogenation pathway.
- Ben-David, Yehoshoa,Diskin-Posner, Yael,Kar, Sayan,Luo, Jie,Milstein, David,Rauch, Michael
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supporting information
p. 1481 - 1487
(2022/03/07)
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- Preparation method of rice borer pheromone component
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The invention provides a preparation method of a rice borer pheromone component, and belongs to the technical field of organic synthesis. The preparation method uses Sodium Hexamethyldisilazane, namely sodium bis(trimethylsilyl)amide as an alkali to obtain relatively high yield, the cis-isomer content is improved, by controlling first wittig reaction at the temperature of -70 DEG C or less and limiting dropwise addition of acetate 12-oxo-dodecyl ester into the reaction system, the problem of increase of trans-type products caused by local overheating of the reaction system can be avoided, andthe reaction yield is improved. The data shows that the yield of the first wittig reaction is 72%, wherein the cis-isomer content is over 97%.
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Paragraph 0061; 0078; 0079
(2019/05/15)
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- Ethyl acetate as an acetyl surrogate for the iodine catalyzed acetylation of alcohols
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The use of readily available ethyl acetate in the presence of iodine as an alternative acetylating agent is reported. Amines and phenols were unreactive under the examined reaction conditions, indicating that the method is highly chemoselective.
- Basumatary, Grace,Bez, Ghanashyam
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supporting information
p. 4312 - 4315
(2017/10/13)
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- Sulfonic acid-functionalized periodic mesoporous organosilicas in esterification and selective acylation reactions
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The application of sulfonic acid-functionalized periodic mesoporous organosilicas (PMOs) having either phenyl (1a) or ethyl (1b) bridging groups was investigated in the esterification of a variety of alcohols and fatty acids. It was found that 1b consistently exhibited higher catalytic performance than 1a in the described reaction. In particular, it was proposed that the superior catalytic activity of 1b in esterification of fatty acids with methanol is a result of adequate hydrophobic-hydrophilic surface balance in the ethyl PMO catalyst. In addition, the study of chemoselective acylation of 1,3-butanediol with dodecanoic acid with varied mesoporous silica-supported solid sulfonic acids including both 1a and 1b implies that there is a compromise between the reaction selectivity and the surface physicochemical properties of the employed catalyst. Our results clearly show that the catalyst having high surface hydrophilic nature gives high selectivity toward the formation of mono-acylated products whereas those with relatively high hydrophobic characteristics showed enhanced selectivity toward the formation of di-acylated products.
- Karimi, Babak,Mirzaei, Hamid M.,Mobaraki, Akbar,Vali, Hojatollah
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p. 3624 - 3631
(2015/07/01)
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- Synthesis of sulfonic acid containing ionic-liquid-based periodic mesoporous organosilica and study of its catalytic performance in the esterification of carboxylic acids
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A new sulfonic acid containing ionic-liquid-based periodic mesoporous organosilica (PMO-IL-SO3H) material was prepared and its catalytic application was investigated in the esterification of carboxylic acids with alcohols. The PMO-IL-SO3H nanocatalyst was first characterized with diffuse reflectance infrared Fourier transform (DRIFT) spectroscopy, transmission electron microscopy (TEM), thermogravimetric analysis (TGA), and nitrogen sorption analysis. Then, the catalytic performance of this material was studied in the esterification of carboxylic acids with short- and long-chain aliphatic alcohols, cyclic alcohols, and benzylic alcohols under solvent-free conditions. The results showed that the catalyst has superior activity for the conversion of several alcohols to afford the corresponding ester products in excellent yields and high purity. Moreover, the catalyst could be recovered and reused several times without a significant decrease in activity and product selectivity. Copyright
- Elhamifar, Dawood,Karimi, Babak,Moradi, Abbas,Rastegar, Javad
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p. 1147 - 1152
(2014/10/16)
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- A simple, general, and highly chemoselective acetylation of alcohols using ethyl acetate as the acetyl donor catalyzed by a tetranuclear zinc cluster
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In the presence of a Zn-cluster catalyst, alcohols are efficiently converted to the corresponding acetate just by refluxing in EtOAc. The mild reaction conditions enabled the reactions of various functionalized alcohols to proceed in good to excellent yield. Moreover, even when a large excess of the acetyl donor is used, the hydroxyl groups are selectively acetylated in the presence of highly nucleophilic aliphatic amino groups, approaching chemoselectivity to that of enzymatic system. Georg Thieme Verlag Stuttgart.
- Iwasaki, Takanori,Maegawa, Yusuke,Hayashi, Yukiko,Ohshima, Takashi,Mashima, Kazushi
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experimental part
p. 1659 - 1663
(2009/12/04)
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- Rapid and efficient method for acetylation of alcohols and phenols with acetic anhydride catalyzed by silica sulfate
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A rapid and efficient method is described for acetylation of a series of alcohols and phenols with acetic anhydride catalyzed by silica sulfate solid acid at room temperature or at refluxing temperature in excellent yield. Copyright Taylor & Francis Group, LLC.
- Jin, Tong-Shou,Zhao, Ying,Liu, Li-Bin,Chen, Zhuo,Li, Tong-Shuang
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p. 1221 - 1227
(2007/10/03)
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- Silica gel-supported phosphotungstic acid (PTA) catalysed acylation of alcohols and phenols with acetic anhydride under mild reaction conditionst
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Phosphotungstic acid, which is commercially available, practically and efficiently catalyses the acylation of a series of alcohols and phenols with acetic anhydride at room temperature of at refluxing temperature.
- Jin, Tong-Shou,Xiao, Jin-Chong,Wang, Zhen-Hua,Li, Tong-Shuang
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p. 412 - 414
(2007/10/03)
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- Reptilian chemistry: volatile compounds from paracloacal glands of the American crocodile (Crocodylus acutus).
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The secretion of the paracloacal glands of the American crocodile (Crocodylus acutus) contains over 80 lipophilic compounds, including saturated and unsaturated long-chain alcohols along with their formic, acetic, and butyric acid esters, and several isoprenoids. Most of these compounds were identified on the basis of mass spectra, obtained by GC-MS. In addition, identification of the major components was supported by infrared spectra obtained by GC-FTIR. Major differences are indicated in the composition of the paracloacal gland secretion of C. acutus and that of another crocodylid, the African dwarf crocodile (Osteolaemus tetraspis).
- Garcia-Rubio, Silvina,Attygalle, Athula B,Weldon, Paul J,Meinwald, Jerrold
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p. 769 - 781
(2007/10/03)
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- Chemoselective acetylation of alcohols, amines, and thiols without catalyst and solvent
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Microwave induced rapid and selective acetylation of alcohols, amines and thiols with acetic anhydride was carried out under non-catalytic and solvent free conditions.
- Bandgar,Kasture,Kamble
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p. 2255 - 2259
(2007/10/03)
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- Evolution of products in the combustion of scrap tires in a horizontal, laboratory scale reactor
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A horizontal laboratory reactor was used to study the evolution of byproducts from the combustion of scrap tires at five nominal temperatures (ranging from 650 to 1050 °C) and different oxygen:sample ratios A model was used to calculate the bulk air ratio (λ), and the oxygen consumption was discussed considering this ratio λ. More than 100 volatile and semivolatile compounds were identified and quantified by gas chromatography mass spectrometry, plotting their yields vs the bulk air ratio and temperature. Five different behaviors considering the bulk air ratio and the temperature were identified.
- Fullana,Font,Conesa,Blasco
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p. 2092 - 2099
(2007/10/03)
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- Catalytic esterification of alcohols, carboxylic acids and transesterification reactions with cerium(IV) triflate
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Esterification reactions of alcohols with acetic, chloroacetic, trifluoroacetic, propionic, stearic, and benzoic acids were catalyzed with Ce(OTf)4 in a solvent or under solvent-free conditions with high yields. The formylation and acetylation of primary and secondary alcohols were also easily achieved in ethyl formate and ethyl acetate. A high retention of the configuration was observed in the acetylation and formylation of (-)-menthol.
- Iranpoor, Nasser,Shekarriz, Marzieh
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p. 455 - 458
(2007/10/03)
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- Selective acetylation of primary alcohols: Acetyl and formyl transfer reactions with copper(II) salts
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The efficient esterification of primary and secondary alcohols in acetic acid was achieved in the presence of Cu(NO3)2. 3H20 in high yields. Selective acetylation of primary in the presence of secondary hydroxyl groups in excellent yields were performed in EtOAc. Formylation of primary and secondary alcohols was also achieved easily in ethyl formate. High retention of configuration was observed in the acetylafion and formylation of (-) menthol in the presence of Cu(NO3)2. 3H20 and Cu(OAC)2. H2O.
- Iranpoor,Firouzabadi,Zolfigol
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p. 1923 - 1934
(2007/10/03)
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- An Extremely Powerful Acylation Reaction of Alcohols with Acid Anhydrides Catalyzed by Trimethylsilyl Trifluoromethanesulfonate
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Trimethylsilyl trifluoromethanesulfonate is an excellent catalyst for the acylation of alcohols with acid anhydrides. Highly functionalized primary, secondary, tertiary, and allylic alcohols, and phenols, were acylated cleanly and efficiently and in a fraction of the time used under the standard DMAP conditions.
- Procopiou, Panayiotis A.,Baugh, Simon P.D.,Flack, Stephen S.,Inglis, Graham G.A.
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p. 2342 - 2347
(2007/10/03)
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- Iodine as an Acetyl Transfer Catalyst
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Iodine catalyses the acetylation of amines, phenols and alcohols, including tertiary ones, with acetic anhydride in excellent yield.
- Borah, Ruli,Deka, Nabajyoti,Sarma, Jadab C.
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p. 110 - 111
(2007/10/03)
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- An extremely fast and efficient acylation reaction of alcohols with acid anhydrides in the presence of trimethylsilyl trifluoromethanesulfonate as catalyst
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Alcohols are converted to esters in a fast, clean and efficient reaction with acid anhydrides in the presence of trimethylsilyl trifluoromethanesulfonate.
- Procopiou, Panayiotis A.,Baugh, Simon P. D.,Flack, Stephen S.,Inglis, Graham G. A.
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p. 2625 - 2626
(2007/10/03)
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