- N-Heterocyclic Carbene Catalyzed Ester Synthesis from Organic Halides through Incorporation of Oxygen Atoms from Air
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Oxygenation reactions with molecular oxygen (O2) as the oxygen source provides a green and straightforward strategy for the construction of O-containing compounds. Demonstrated here is a novel N-heterocyclic carbene (NHC) catalyzed oxidative transformation of simple and readily available organic halides into valuable esters through the incorporation of O-atoms from O2. Mechanistic studies prove that the deoxy Breslow intermediate generated in situ is oxidized to a Breslow intermediate for further transformation by this oxidative protocol. This method broadens the field of NHC catalysis and promotes oxygenation reactions with O2.
- Tan, Hui,Wang, Shen-An,Yan, Zixi,Liu, Jianzhong,Wei, Jialiang,Song, Song,Jiao, Ning
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p. 2140 - 2144
(2020/12/01)
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- Epoxide as precatalyst for metal-free catalytic transesterification
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Transesterification of methyl esters was accelerated by an in situ-generated metal-free catalyst comprising a quaternary alkylammonium salt and an epoxide. The combination of a quaternary alkylammonium acetate and glycidol is optimal, and various esters were synthesized from methyl esters with alcohols in good to excellent yield. Analysis of the catalyst solution revealed that basic species are generated by the ring-opening reaction of epoxide.
- Tanaka, Shinji,Nakashima, Takuya,Satou,Oono, Hiromi,Kon, Yoshihiro,Tamura, Masanori,Sato, Kazuhiko
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p. 2009 - 2013
(2019/07/03)
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- Preparation method for synthesizing ester compound by using N-Boc amide as raw material
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The invention relates to a preparation method for synthesizing an ester compound by using N-Boc amide as a raw material. According to the method, an inorganic base is used as a catalyst; the N-Boc amide is subjected to an intermolecular nucleophilic substitution reaction with various alcohol compounds; and various ester compounds can be efficiently obtained. The method has the advantages of beingmild in reaction condition, simple and convenient to operate, high in yield and favorable in functional-group compatibility.
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Paragraph 0027; 0028
(2019/03/28)
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- Cesium Carbonate Catalyzed Esterification of N-Benzyl- N-Boc-amides under Ambient Conditions
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We report a general activated amide to ester transformation catalyzed by Cs2CO3. Using this approach, esterification proceeds under relatively mild conditions and without the need for a transition metal catalyst. This method exhibits broad substrate scope and represents a practical alternative to existing esterification strategies. The synthetic utility of this protocol is demonstrated via the facile synthesis of crown ether derivatives and the late-stage modification of a representative natural product and several sugars in reasonable yields.
- Ye, Danfeng,Liu, Zhiyuan,Chen, Hao,Sessler, Jonathan L.,Lei, Chuanhu
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supporting information
p. 6888 - 6892
(2019/09/07)
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- Base-free oxidation of alcohols to esters at room temperature and atmospheric conditions using nanoscale Co-based catalysts
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The direct oxidation of alcohols to esters with molecular oxygen is an attractive and crucial process for the synthesis of fine chemicals. To date, the heterogeneous catalyst systems that have been identified are based on noble metals or have required the addition of base additives. Here, we show that Co nanoparticles embedded in nitrogen-doped graphite catalyze the aerobic oxidation of alcohols to esters at room temperature under base-free and atmospheric conditions. Our Co@C-N catalytic system features a broad substrate scope for aromatic and aliphatic alcohols as well as diols, giving their corresponding esters in good to excellent yields. This apparently environmentally benign process provides a new strategy with which to achieve selective oxidation of alcohols.
- Zhong, Wei,Liu, Hongli,Bai, Cuihua,Liao, Shijun,Li, Yingwei
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p. 1850 - 1856
(2015/03/14)
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- Graphite oxide as an efficient solid reagent for esterification reactions
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Esterification of organic acids with alcohols under mild conditions in high yields using graphite oxide, a readily available and inexpensive material, as an effective reagent is described.
- Mirza-Aghayan, Maryam,Rahimifard, Mahshid,Boukherroub, Rabah
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p. 859 - 864
(2014/12/10)
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- Generally applicable and efficient esterification of aldehydes with alcohols catalyzed by cyclopalladated ferrocenylimine
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The palladacycle-catalyzed esterification of a variety of aldehydes with alcohols was developed. This reaction allows formation of esters in moderate to excellent yields not only for various aldehydes but also alcohols. In addition, the esterification could proceed well under mild conditions with a low catalyst loading of 0.0625 mol%. Copyright
- Ma, Gaizhi,Leng, Yuting,Qiao, Huijie,Yang, Fan,Wang, Shiwei,Wu, Yangjie
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- Synthesis of symmetric diester-functionalised Troeger's base analogues
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The yields of ester-functionalised Troeger's base analogues are dramatically improved by incorporating an electron-donating group on the aromatic ring and/or enhancing solubil- ity of the aniline unit. In addition to 2,8-diester compounds, 1,7-, 3,9- and 4,10-diester-functionalised Troeger's base analogues have been prepared for the first time.
- Bhuiyan, M. Delower H.,Zhu, Kai-Xian,Jensen, Paul,Try, Andrew C.
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supporting information; experimental part
p. 4662 - 4670
(2010/10/19)
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- Effective esterification of carboxylic acids using (6-oxo-6H-pyridazin-1-yl)phosphoric acid diethyl ester as novel coupling agents
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(6-Oxo-6H-pyridazin-1-yl)phosphoric acid diethyl esters (3) are efficient and selective coupling agents for equimolar esterification of carboxylic acids and alcohols. Esterification of aliphatic and aromatic carboxylic acids with aliphatic and aromatic alcohols using 3 afforded the corresponding esters chemoselectively in good to excellent yield.
- Won, Ju-Eun,Kim, Ho-Kyun,Kim, Jeum-Jong,Yim, Heong-Seup,Kim, Min-Jung,Kang, Seung-Beom,Chung, Hyun-A.,Lee, Sang-Gyeong,Yoon, Yong-Jin
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p. 12720 - 12730
(2008/03/14)
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- Efficient and simple NaBH4 reduction of esters at cationic micellar surface
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(Chemical Equation Presented) A simple, efficacious, and biocompatible methodology for reducing esters with sodium borohydride at an aqueous cationic micellar surface under ambient conditions has been developed. The present method holds promise for future use in selective functional group reduction and stereocontrolled alcohol synthesis.
- Das, Debapratim,Roy, Sangita,Das, Prasanta Kumar
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p. 4133 - 4136
(2007/10/03)
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- Smectogenic Salts Formed by Combination of Alkyl p-Aminobenzoates and p-Ethyl- or p-Chlorobenzenesulfonic Acid
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Two series of smectogenic salts were obtained by combining alkyl p-aminobenzoates with p-ethyl- and p-chlorobenzenesulfonic acids, respectively.The shortest ester alkyl chain required to generate a smectic A phase is nonyl when the former sulfonic acid is employed but the chain may be as short as butyl when the latter is employed.The smectic A-isotropic transition temperature in the second series is significantly higher than that in the first series, indicating that the terminal substituent on the anion is as crucial as that in non-ionic mesogens in determining the mesophase stability. - Keywords: Smectic, alkyl p-aminobenzoates, benzenesulfonates
- Matsunaga, Y.,Sakamoto S.,Togashi, A.,Tsujimoto, M.
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p. 161 - 166
(2007/10/02)
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- EFFECTS OF BRANCHING OF THE ALKYL CHAIN ON THE LIQUID CRYSTALLINE PROPERTIES OF N-(p-PHENYLBENZYLIDENE)-p-ALKOXYCARBONYLANILINES.
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The liquid crystal behavior of twenty-three N-(p-phenylbenzylidene)-p-alkoxycarbonylanilines has been examined by optical microscopy and differential scanning calorimetry in order to study the effects of branching of the alkyl groups.
- Matsunaga,Miyajima
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p. 353 - 359
(2007/10/02)
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