- Synthesis of the first difunctional N-fluoro perfluoroalkylsulfonylimides, CF3SO2NFSO2(CF2) nSO2NFSO2CF3
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Synthesis of difunctional N,N′-difluoro perfluoroalkylsulfonamides, n = 4, 6 is reported. A related compound with an oxygen linkage CF3SO2NFSO2(CF2)2O(CF2)2SO2NFSOsub
- Zhang, Jie,DesMarteau, Darryl D,Zuberi, Sharique,Ma, Jing-Ji,Xue, Lixin,Gillette, Samuel M,Blau, Hanne,Gerhardt, Rolf
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Read Online
- Synthesis and comparison of N-fluorobis[(perfluoroalkyl)sulfonyl]imides with different perfluoroalkyl groups
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N-fluorobis[(perfluoroalkyl)sulfonyl]imides, CF3SO2N(F)SO2Rf (Rf′=C4F9, C6F13, C8F17) and (C4F9SO2)2NF, were prepared by direct fluorination of corresponding N-H compounds using elemental fluorine without a solvent in good to excellent yields. All of these N-F compounds are electrophilic fluorination agents and can easily deliver F+ to certain molecules. Their reactions with aromatic rings, beta-diketones, and alkenes were investigated to compare their fluorination power.
- Zhang, Jie,Desmarteau, Darryl D.
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Read Online
- Recyclable cinchona alkaloid catalyzed asymmetric Michael addition reaction
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A highly enantioselective and diastereoselective Michael addition reaction of α-fluoro-β-ketoesters with maleimides is catalyzed by fluorous cinchona alkaloid to afford two adjacent chiral centers. The catalyst attached with a perfluroalkyl tag can be rec
- Huang, Xin,Yi, Wen-Bin,Ahad, Danash,Zhang, Wei
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Read Online
- A Pd-Catalyzed [4 + 2] Annulation Approach to Fluorinated N-Heterocycles
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3-Fluoro- and trifluoromethylthio-piperidines represent important building blocks for discovery chemistry. We report a simple and efficient method to access analogs of these compounds that are armed with rich functionality allowing them to be chemoselectively derivatized with high diastereocontrol.
- García-Vázquez, Víctor,Hoteite, Larry,Lakeland, Christopher P.,Watson, David W.,Harrity, Joseph P. A.
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supporting information
p. 2811 - 2815
(2021/05/05)
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- Gold-catalyzed Fluorination of Alkynyl Esters and Ketones: Efficient Access to Fluorinated 1,3-Dicarbonyl Compounds
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We developed an efficient synthesis of 2-fluoro-1,3-dicarbonyl compounds using readily available alkynyl ketones or esters as starting material. The key step is the insertion of hydrogen fluoride (HF) to the gold carbene intermediate generated from cationic gold catalyzed addition of N-oxides to alkynyl ketones or esters. This method gives excellent chemical yields and regioselectivity with good functional group tolerance. (Figure presented.).
- Zeng, Xiaojun,Lu, Zhichao,Liu, Shiwen,Hammond, Gerald B.,Xu, Bo
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supporting information
p. 4062 - 4066
(2017/11/30)
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- 2-fluoro -1,3-dicarbonyl compounds of manufacturing method
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PROBLEM TO BE SOLVED: To provide a method of producing 2-fluoro-1,3-dicarbonyl compounds useful as synthetic intermediates of electronic material ingredients and medical and agricultural compounds, which provides a high yield and high selectivity.SOLUTION
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Paragraph 0036; 0054; 0061-0063
(2016/11/21)
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- A facile and mild approach for stereoselective synthesis of α-fluoro-α,β-unsaturated esters from α-fluoro-β-keto esters via deacylation
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The highly stereoselective olefination reaction of α-fluoro-β-keto esters for the synthesis of α-fluoro-α,β-unsaturated esters has been developed. The olefination combines nucleophilic addition, intramolecular nucleophilic addition, and elimination in one step, as well as provides a facile synthetic approach to α-fluoro-α,β-unsaturated esters which are important units in many biologically active compounds and useful precursors in a variety of functional-group transformations.
- Qian, Jinlong,Yi, Wenbin,Lv, Meifang,Cai, Chun
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supporting information
p. 127 - 132
(2015/02/02)
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- Facile synthesis of 2-fluoro-1,3-dicarbonyl compounds with aqueous hydrofluoric acid mediated by iodosylarenes
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Direct fluorination of 1,3-dicarbonyl compounds including 1,3-diketones, 3-oxo esters, and 3-oxoamides was conducted using aqueous hydrofluoric acid with the aid of iodosylarenes, giving the corresponding 2-fluorinated products in good to high yields. Among the used iodosylarenes, o-iodosyltoluene was found to be the most effective, and the yield of 2-fluorinated products was improved. Georg Thieme Verlag Stuttgart New York.
- Kitamura, Tsugio,Kuriki, Satoshi,Muta, Kensuke,Morshed, Mohammad Hasan,Muta, Kazutaka,Gondo, Keisuke,Hori, Yuji,Miyazaki, Masaya
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p. 3125 - 3130
(2013/12/04)
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- Catalytic fluorination of 1,3-dicarbonyl compounds using iodoarene catalysts
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Catalytic fluorination of 1,3-dicarbonyl compounds with aqueous hydrofluoric acid proceeded efficiently with the aid of iodoarene catalysts in the presence of m-CPBA as a terminal oxidant. o-Iodotoluene, o-iodoanisole, and o-ethyliodobenzene showed a high
- Kitamura, Tsugio,Muta, Kazutaka,Kuriki, Satoshi
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p. 6118 - 6120
(2013/10/22)
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- One-pot fluorination and asymmetric Michael addition promoted by recyclable fluorous organocatalysts
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A novel one-pot fluorination and asymmetric Michael addition reaction sequence promoted by recyclable fluorous bifunctional cinchona alkaloid-thiourea organocatalysts is introduced for the synthesis of α-fluoro-β- ketoesters bearing two chiral centers.
- Yi, Wen-Bin,Zhang, Zijuan,Huang, Xin,Tanner, Angela,Cai, Chun,Zhang, Wei
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p. 18267 - 18270
(2013/10/21)
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- Reaction of iodonium ylides of 1,3-dicarbonyl compounds with HF reagents
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Reaction of dibenzoylmethane with (diacetoxyiodo)benzene in the presence of KOH in MeCN quantitatively gave the corresponding iodonium ylide, which was treated with a HF reagent to afford the corresponding 2-fluorinated dibenzoylmethane in 14-50% yields.
- Gondo, Keisuke,Kitamura, Tsugio
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experimental part
p. 6625 - 6632
(2012/08/27)
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- One-pot fluorination followed by Michael addition or Robinson annulation for preparation of α-fluorinated carbonyl compounds
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Fluorination followed by the Michael addition or Robinson annulation of 1,3-dicarbonyl compounds is introduced for the synthesis of acyclic and cyclic α-fluoro-β-ketoesters and α-fluoro-1,3-diketones. The decarboxylation step can also be added to the reac
- Yi, Wen-Bin,Cai, Chun,Huang, Xin,Zhang, Wei
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p. 3185 - 3189,5
(2020/09/16)
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- A practical and convenient fluorination of 1,3-dicarbonyl compounds using aqueous HF in the presence of iodosylbenzene
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Chemical equations presented. A simple, practical, and convenient fluorination of 1,3-dicarbonyl compounds was achieved by direct use of aqueous hydrofluoric acid and iodosylbenzene (PhIO). The reaction of ethyl benzoylacetate with the reagent system of a
- Kitamura, Tsugio,Kuriki, Satoshi,Morshed, Mohammad Hasan,Hori, Yuji
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supporting information; experimental part
p. 2392 - 2394
(2011/06/28)
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- N-Fluorobisimides. Efficient reagents for the fluorination of 1,3-dicarbonyl derivatives
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Fluorination of 1,3-dicarbonyl derivatives with N-fluorobisimides, (CF3SO2)2NF (1), results in the formation of 2-fluoro- or 2,2-difluoro-1,3-dicarbonyl analogs, depending on the reaction conditions.High yields are obtained for a variety of structural types.In the case of 1,3-dicarbonyl derivatives with low enol content, only the sodium enolates react with 1.Thus 1 has been demonsrtated to be perhaps the best fluorinating reagent for the fluorination of 1,3-dicarbonyl derivatives.All of the 2-fluoro-1,3-dicarbonyl products exist predominantly as keto tautomers.
- Xu, Ze-Qi,DesMarteau, Daryl D.,Gotoh, Yoshihiko
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- N-Fluoro Perfluoroalkylsulphonimides: Efficient Reagents for the Fluorination of 1,3-Dicarbonyl Derivatives
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Fluorination of 1,3-dicarbonyl derivatives with N-fluoro sulphonimides afforded either 2-fluoro or 2,2-difluoro products in high yields.
- Xu, Ze-Qi,DesMarteau, Darryl D.,Gotoh, Yoshihiko
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p. 179 - 181
(2007/10/02)
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