Sodium dithionite initiated reaction of pent-4-en-1-amines with fluoroalkyl iodides for the synthesis of 2-fluoroalkyl pyrrolidine derivatives

Zhu Y.; Yeng X.; Fang X.; Yang X.; Ye L.; Cai W.; Zhang Y.; Wu F.

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Sodium dithionite initiated reaction of pent-4-en-1-amines with fluoroalkyl iodides for the synthesis of 2-fluoroalkyl pyrrolidine derivatives

机译：亚连二硫酸钠引发的戊-4-烯-1-胺与氟代烷基碘的反应，用于合成2-氟代烷基吡咯烷衍生物

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Pent-4-en-1-amines are reactive to fluoroalkyl iodides with respect to sodium dithionite initiated free radical addition reactions. We report here the development of a novel and efficient synthesis of 2-fluoroalkyl pyrrolidine derivatives by sodium dithionite initiated one-pot reaction of pent-4-en-1-amines bearing various protecting groups with fluoroalkyl iodides. Among which, the N-benzyl-pent-4-en-1-amine exhibited the best tolerance toward the reaction condition in the present study, affording the desired adducts 3 in moderate to good yields of 65-85%.

机译：关于连二亚硫酸钠引发的自由基加成反应，Pent-4-en-1-胺与氟代烷基碘有反应性。我们在这里报告通过连二亚硫酸钠引发的新型有效合成2-氟烷基吡咯烷衍生物的开发，该合成引发了带有各种保护基团的五-4-烯-1-胺与氟代烷基碘的一锅法反应。其中，N-苄基-戊-4-烯-1-胺在本研究中显示出对反应条件的最佳耐受性，以中度至良好的收率65-85％提供了所需的加合物3。

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《Tetrahedron》 |2011年第6期|共7页
作者
Zhu Y.; Yeng X.; Fang X.; Yang X.; Ye L.; Cai W.; Zhang Y.; Wu F.;
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正文语种 eng
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关键词
2-Fluoroalkyl pyrrolidine; Fluoroalkyl iodide; Free radical addition-intramolecular nucleophilic substitution; Pent-4-en-1-amine;

机译：2-氟烷基吡咯烷;氟烷基碘;自由基加成-分子内亲核取代;Pent-4-en-1-胺;

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1. Sodium dithionite initiated reaction of pent-4-en-1-amines with fluoroalkyl iodides for the synthesis of 2-fluoroalkyl pyrrolidine derivatives [J] . Zhu Y., Yeng X., Fang X., Tetrahedron . 2011,第6期

机译：亚连二硫酸钠引发的戊-4-烯-1-胺与氟代烷基碘的反应，用于合成2-氟代烷基吡咯烷衍生物
2. Sodium dithionite initiated addition of CF2Br2 to beta-pinene and reactions of the adduct Synthesis and the reactivity of new 1,1-difluorodienes [J] . Wojciech Dmowski, Anna Jalmuzna, Z.Urbanczyk-Lipkowska Journal of Fluorine Chemistry . 2007,第12期

机译：连二亚硫酸钠引发的CF2Br2向β-pine烯的加成反应以及加合物的反应新的1,1-二氟二烯的合成和反应性
3. Sodium dithionite initiated reactions of Halothane with enol ethers Facile synthesis of 3-trifluoromethyl substituted vinyl carbonyl compounds [J] . Halina Plenkiewicz, Wojciech Dmowski, Miroslaw Lipinski Journal of Fluorine Chemistry . 2001,第2期

机译：连二亚硫酸钠引发氟烷与烯醇醚的反应轻松合成3-三氟甲基取代的乙烯基羰基化合物
4. Enantioselective Synthesis of Bicyclic Pyrrolidine Derivatives via One-Pot Organo and Palladium Catalysis [C] . Bijan Mohon Chaki, Jianfei Bai, Kazuhiro Takenaka 日本化学会春季年会講演予稿集 . 2018

机译：通过单盆机构和钯催化对双环吡咯烷衍生物的映选择性合成
5. Applications of samarium(II) iodide-promoted 8-membered ring cyclization reactions in natural product total synthesis: I. The total synthesis of (+)-isoschizandrin. II. Progress toward the total synthesis of variecolin. [D] . George, Kelly M. 2005

机译：碘化sa（II）促进的8元环环化反应在天然产物总合成中的应用：I.（+）-异五味子的总合成。二。向水杨素的全合成进展。
6. Reactions of cytochrome c oxidase with sodium dithionite. [O] . G D Jones, M G Jones, M T Wilson, 1983

机译：细胞色素C氧化酶与连二亚硫酸钠的反应。
7. Synthesis and Characterization of Novel SF5 Containing Fluoroalkyl Iodides and Derivatives [O] . Julia Renn 2000

机译：含氟烷基碘化物和衍生物新型SF5的合成与表征

Sodium dithionite initiated reaction of pent-4-en-1-amines with fluoroalkyl iodides for the synthesis of 2-fluoroalkyl pyrrolidine derivatives

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