102-16-9Relevant articles and documents
Preparation of acyl fluorides with hydrogen fluoride-pyridine and 1,3-dicyclohexylcarbodiimide
Chen, Chinpiao,Chien, Chin-Tzu,Su, Chu-Hsiang
, p. 75 - 77 (2002)
This work presents an efficient procedure for preparing acyl fluorides by simply reacting carboxylic acid with hydrogen fluoride-pyridine and 1,3-dicyclohexylcarbodiimide (DCC) in dichloromethane. The acyl fluorides were converted in situ to the corresponding benzyl carboxylic esters by adding benzyl alcohol and triethylamine to the reaction mixture.
Efficient esterification of carboxylic acids with alkyl halides catalyzed by fluoride ions in ionic liquids
Brinchi,Germani,Savelli
, p. 6583 - 6585 (2003)
Ionic liquids based on 1,3-dialkylimidazolinium methanesulfonate have been used as efficient reusable reaction media in the esterification of several carboxylic acids with alkyl halides catalyzed by fluoride ions. The method has wide applicability, and it is mild and green; it is useful for the protection of acids, via ester formation, for alkali labile molecules.
S,S-Bis Dithiocarbonate. A New Reactive Coupling Agent for the Direct Esterification of Carboxylic Acids
Kim, Sunggak,Kim, Sung Soo
, p. 1017 - 1019 (1986)
S,S-Bis dithiocarbonate, prepared from 4,6-dimethyl-2-pyrimidinethiol hydrochloride and phosgene in the presence of triethylamine in dichloromethane/toluene, is a new reactive coupling agent for the direct esterification of carboxylic acids with alcohols.
Use of diethoxymethane as a solvent for phase-transfer esterification of carboxylic acids
Coleman, M. Todd
, p. 1911 - 1913 (2012)
The esterification of carboxylic acids with selected primary alkyl halides in diethoxymethane (DEM) utilizing solid-liquid phase-transfer catalysis has been studied. The use of DEM as the solvent simplifies the process in that a single solvent can be used for both reaction and workup.
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Williams,K.,Halpern,B.
, p. 727 - 728 (1974)
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One-electron Oxidation of Carboxylates by Hexachloroosmate(V) Ion
Eberson, Lennart,Nilsson, Monica
, p. 1041 - 1042 (1992)
Hexachloroosmate(V) cleanly oxidizes tetrabutylammonium tert-butylcyanoacetate to decarboxylative-coupling products, meso- and rac-2,3-di-tert-butylsuccinonitrile, thus constituting the first metal ion-based oxidant to be found to simulate properly this aspect of the Kolbe anodic oxidation of carboxylates.
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Inomata et al.
, p. 1866 (1978)
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Mercury(II) Oxide/Tetrafluoroboric Acid; A General Method for Esters from Carboxylic Acids and Alkyl Halides
Barluenga, Jose,Alonso-Cires, Luisa,Campos, Pedro, J.,Asensio, Gregorio
, p. 649 - 651 (1983)
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Palladium-catalyzed carbonylation of benzyl alcohol and its analogs promoted by HI in aqueous systems
Lin, Yong-Shou,Yamamoto, Akio
, p. 3747 - 3750 (1997)
Carbonylation of benzyl alcohol catalyzed by a palladium(0) complex and promoted by hydrogen iodide gives phenylacetic acid in excellent yields in aqueous systems. The catalysis is proposed to proceed through a benzylpalladium species formed by the oxidative addition of benzyl iodide, produced in situ by the interaction of benzyl alcohol with HI, to a Pd(0) species. Application of the carbonylation process to other arylmethanol analogs provided convenient means to prepare 3-isochromanone, 1,4-benzenediacetic acid, 2-hydroxybenzeneacetic acid and 2-naphthaleneacetic acid.
Electrochemically Enabled, Nickel-Catalyzed Dehydroxylative Cross-Coupling of Alcohols with Aryl Halides
Li, Zijian,Sun, Wenxuan,Wang, Xianxu,Li, Luyang,Zhang, Yong,Li, Chao
supporting information, p. 3536 - 3543 (2021/03/08)
As alcohols are ubiquitous throughout chemical science, this functional group represents a highly attractive starting material for forging new C-C bonds. Here, we demonstrate that the combination of anodic preparation of the alkoxy triphenylphosphonium ion and nickel-catalyzed cathodic reductive cross-coupling provides an efficient method to construct C(sp2)-C(sp3) bonds, in which free alcohols and aryl bromides - both readily available chemicals - can be directly used as coupling partners. This nickel-catalyzed paired electrolysis reaction features a broad substrate scope bearing a wide gamut of functionalities, which was illustrated by the late-stage arylation of several structurally complex natural products and pharmaceuticals.
Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes
Roy, Sourav,Kumar, Gourav,Chatterjee, Indranil
supporting information, p. 6709 - 6713 (2021/09/08)
A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.