N,N-diethyl iododifluoroacetamide | 127427-41-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N-diethyl iododifluoroacetamide
• 英文别名: ICF2CONEt2；N,N-diethyl-2,2-difluoro-2-iodoacetamide
• CAS: 127427-41-2
• 化学式: C₆H₁₀F₂INO
• 分子量: 277.053
• InChiKey: UBCMUBUKEZNPSG-UHFFFAOYSA-N

物化性质

• 沸点：
  234.8±40.0 °C(Predicted)
• 密度：
  1.713±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-diethyl iododifluoroacetamide 在 铜 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以75%的产率得到C₁₂H₂₀F₄N₂O₂
  参考文献：
  名称：

  Copper-Mediated Fluoroalkylation Reactions with Iododifluoroacetamides: Controlling the Selectivity among Cross-Coupling, Intramolecular Cyclization, and Homocoupling Reactions

  摘要：

  Cu-mediated fluoroalkylation reactions with iododifluoroacetamides I have been systematically investigated. It was found that three types of reactions may coexist in Cu-mediated reactions between iododifluoroacetamides and aryl/alkenyl iodides: cross-coupling, intramolecular cyclization, and homocoupling reactions. The selectivity among these three types of reactions could be controlled by tuning the substituents on the nitrogen atom of iododifluoroacetamides, and/or by removing the cross-coupling reaction partner (aryl/alkenyl halides). The general rule is as follows: (a) in the presence of proper aryl/alkenyl iodides, the cross-coupling products 2 (or 6) are generally formed as the major products; (b) in the absence of aryl/alkenyl iodides, and when R-1 = alkyl and R-2 = aryl groups, or when R-1 = R-2 = aryl groups, the intramolecular cyclization products 3 can be formed predominantly; and (c) in the absence of aryl/alkenyl iodides, and when R-1 = R-2 = alkyl groups, or when R-1 = H and R-2 = alkyl, aryl groups, the homocoupling products 4 can be formed dominantly. Our experimental results also indicate that in many cases when cross-coupling, homocoupling, and intramolecular cyclization reactions coexist in the Cu-mediated reaction system, the reactivity decreases in the following order: cross-coupling > intramolecular cyclization > homocoupling.

  DOI：

  10.1021/jo1005262
• 作为产物：
  描述：

  2-(diethylamino)-1, 1-difluoro-2-oxoethanesulfonylfluoride 在 水 、 碳酸氢钠 、 sodium sulfite 、 碘 、 potassium iodide 作用下， 以 水 为溶剂， 反应 4.0h， 以58%的产率得到N,N-diethyl iododifluoroacetamide
  参考文献：
  名称：

  Copper-Mediated Fluoroalkylation Reactions with Iododifluoroacetamides: Controlling the Selectivity among Cross-Coupling, Intramolecular Cyclization, and Homocoupling Reactions

  摘要：

  Cu-mediated fluoroalkylation reactions with iododifluoroacetamides I have been systematically investigated. It was found that three types of reactions may coexist in Cu-mediated reactions between iododifluoroacetamides and aryl/alkenyl iodides: cross-coupling, intramolecular cyclization, and homocoupling reactions. The selectivity among these three types of reactions could be controlled by tuning the substituents on the nitrogen atom of iododifluoroacetamides, and/or by removing the cross-coupling reaction partner (aryl/alkenyl halides). The general rule is as follows: (a) in the presence of proper aryl/alkenyl iodides, the cross-coupling products 2 (or 6) are generally formed as the major products; (b) in the absence of aryl/alkenyl iodides, and when R-1 = alkyl and R-2 = aryl groups, or when R-1 = R-2 = aryl groups, the intramolecular cyclization products 3 can be formed predominantly; and (c) in the absence of aryl/alkenyl iodides, and when R-1 = R-2 = alkyl groups, or when R-1 = H and R-2 = alkyl, aryl groups, the homocoupling products 4 can be formed dominantly. Our experimental results also indicate that in many cases when cross-coupling, homocoupling, and intramolecular cyclization reactions coexist in the Cu-mediated reaction system, the reactivity decreases in the following order: cross-coupling > intramolecular cyclization > homocoupling.

  DOI：

  10.1021/jo1005262

文献信息

• Visible Light-Promoted Phosphine-Catalyzed Difluoroalkylation of Arenes and Heterocycles
  作者：Heng Lu、Dong-yu Wang、Ao Zhang

  DOI：10.1021/acs.joc.9b02882

  日期：2020.1.17

  A visible light-promoted difluoroalkylation reaction of arenes or heterocycles, using triaryl phosphine as the catalyst and difluoroalkyl iodide as the alkylating agent, is presented. The strategy is highlighted by photocatalyst-free, mild reaction conditions and a broad substrate scope. Mechanistic experiments indicate that this reaction involves a radical-chain process that is initiated by an electron

  提出了使用三芳基膦作为催化剂和二氟烷基碘化物作为烷基化剂的芳烃或杂环的可见光促进的二氟烷基化反应。无光催化剂，温和的反应条件和广泛的底物范围突出了该策略。机理实验表明，该反应涉及自由基链过程，该自由基链过程由二氟烷基碘和膦形成的电子供体-受体配合物引发。
• Nickel‐Catalyzed Carbofluoroalkylation of 1,3‐Enynes to Access Structurally Diverse Fluoroalkylated Allenes
  作者：Kai‐Fan Zhang、Kang‐Jie Bian、Chao Li、Jie Sheng、Yan Li、Xi‐Sheng Wang

  DOI：10.1002/anie.201813184

  日期：2019.4

  A nickel‐catalyzed 1,4‐carbofluoroalkylation of 1,3‐enynes to access structurally diverse fluoroalkylated allenes has been established. This method has demonstrated high catalytic reactivity, mild reaction conditions, broad substrate scope, and excellent functional‐group tolerance. The key to success is the use of a nickel catalyst to generate different fluoroalkyl radicals from readily available and

  已经建立了镍催化的1,3-炔烃的1,4-碳氟烷基化反应，以获取结构多样的氟代烷基化的烯。该方法显示出高催化活性，温和的反应条件，广泛的底物范围和出色的官能团耐受性。成功的关键是使用镍催化剂从容易获得的，结构多样的氟代烷基卤化物中生成不同的氟代烷基自由基，并通过自由基中继剂获得1,3-炔的1,4-二官能化。该策略提供了结构多样的多取代的烯的简便合成，并提供了用于批量生产各种氟化生物活性分子以通过进一步转化发现药物的解决方案。
• Fluoroalkylation–Borylation of Alkynes: An Efficient Method To Obtain (<i>Z</i>)-Tri- and Tetrasubstituted Fluoroalkylated Alkenylboronates
  作者：Wen-Hao Guo、Hai-Yang Zhao、Zhi-Ji Luo、Shu Zhang、Xingang Zhang

  DOI：10.1021/acscatal.8b02842

  日期：2019.1.4

  Efficient methods for the synthesis of fluoroalkylated alkenylboronates are very limited, despite their importance in modern organic synthesis. Herein, we report a palladium-catalyzed trans-fluoroalkylation–borylation of alkynes with fluoroalkyl iodides and B2pin2. The reaction tolerates a series of difluoroalkyl iodides and perfluoroalkyl iodides and can enable coupling with a variety of alkynes,

  尽管在现代有机合成中很重要，但合成氟烷基化烯基硼酸酯的有效方法非常有限。在本文中，我们报道了炔烃与氟代烷基碘化物和B 2 pin 2的钯催化反式-氟代烷基化-硼化。该反应可耐受一系列二氟烷基碘和全氟烷基碘，并且可以与各种炔烃偶联，包括内部和末端炔烃，具有高效，高官能团相容性以及高区域选择性和立体选择性。初步的机理研究表明，反式氟烷基化的烯基碘是关键中间体，其随后进行硼酸酯化以产生反式氟烷基化的烯基硼酸酯。
• Copper-Mediated Aerobic Fluoroalkylation of Arylboronic Acids with Fluoroalkyl Iodides at Room Temperature
  作者：Qingqing Qi、Qilong Shen、Long Lu

  DOI：10.1021/ja301705z

  日期：2012.4.18

  A Cu-mediated ligandless aerobic fluoroalkylation of arylboronic acids under mild conditions is described for the first time. The reaction tolerates a wide range of functional groups, allowing for further transformation. Mechanistic studies suggest that [R(f)Cu] is the active Cu species that forms the desired perfluoroalkylarenes and that [R(f)Cu] is generated from [PhCu] by either an oxidative addition/reductive

  首次描述了在温和条件下 Cu 介导的无配体有氧氟烷基化芳基硼酸。该反应耐受范围广泛的官能团，允许进一步转化。机理研究表明，[R(f)Cu] 是形成所需全氟烷基芳烃的活性铜物质，[R(f)Cu] 是通过氧化加成/还原消除机制或通过亲核取代从 [PhCu] 生成的卤素“吃了”中间体。
• Phototriggered Fluoroalkylation/Cyclization of Unactivated 1-Acryloyl-2-cyanoindoles: Synthesis of RCOCF₂-Substituted Pyrrolo[1,2-<i>a</i>]indolediones
  作者：Weixian Lv、Pengyuan Yang、Jinwei Yuan、Jiayi Li、Mengran Liang、Yitong Liu、Dongliang Xing、Liangru Yang

  DOI：10.1021/acs.joc.3c02986

  日期：2024.3.1

  A photochemical approach toward RCOCF2-substituted pyrrolo[1,2-a]indolediones was developed by the radical cascade difluoroalkylation/cyclization reaction of unactivated 1-acryloyl-2-cyanoindoles with ethyl iododifluoroacetate or iododifluoramides under visible-light irradiation. This transition-metal- and photosensitizer-free protocol afforded diverse difluoroalkylated pyrrolo[1,2-a]indolediones in

  通过未活化的1-丙烯酰基-2-氰基吲哚与碘二氟乙酸乙酯或碘二氟酰胺在可见光照射下的自由基级联二氟烷基化/环化反应，开发了一种制备RCOCF 2 -取代的吡咯并[ 1,2 -a]吲哚二酮的光化学方法。这种不含过渡金属和光敏剂的方案在温和的反应条件下以中等至良好的收率提供了多种二氟烷基化吡咯并[1,2- a ]吲哚二酮。最吸引人的是，该反应可以在阳光照射下顺利进行，这为二氟烷基化吡咯并[1,2- a ]吲哚二酮开辟了一条新途径。