(iododifluoromethyl)trimethylsilane | 1616058-46-8

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: (iododifluoromethyl)trimethylsilane
• 英文别名: [Difluoro(iodo)methyl]-trimethylsilane
• CAS: 1616058-46-8
• 化学式: C₄H₉F₂ISi
• 分子量: 250.102
• InChiKey: QVNBJMBBKQVLPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-methoxybenzylidene)-N-methyl-1-phenylmethanaminium trifluoromethanesulfonate 、 (iododifluoromethyl)trimethylsilane 在 N,N-二甲基丙烯基脲 、 四丁基碘化铵 作用下， 反应 2.0h， 以156.1 mg的产率得到benzyl[2,2-difluoro-2-iodo-1-(4-methoxyphenyl)ethyl]methylamine
  参考文献：
  名称：

  Nucleophilic Bromodifluoromethylation of Iminium Ions

  摘要：

  A method for bromodifluoromethylation of iminium ions using Me3SiCF2Br is described. The reaction involves room temperature activation of the silicon reagent by HMPA to generate difluorocarbene, which upon interacting with excess of bromide ion provides bromodifluoromethyl carbanionic species. The iminium electrophiles are generated in situ from aldehydes, secondary amines, proton sponge, and silyl triflate. The reaction can be extended for introduction of chlorodifluoromethyl and iododifluoromethyl groups.

  DOI：

  10.1021/jo501644m
• 作为产物：
  描述：

  [difluoro(trimethylsilyl)methyl]zinc bromide 在 碘 作用下， 反应 18.2h， 以4.31 g的产率得到(iododifluoromethyl)trimethylsilane
  参考文献：
  名称：

  醛的亲核溴和碘二氟甲基化

  摘要：

  描述了使用溴和碘取代的二氟甲基硅试剂（Me 3 SiCF 2 X）进行醛的溴和碘二氟甲基化的方法。该反应在丙腈中四丁基铵和锂盐Bu 4 NX / LiX（X = Br或I）的组合存在下进行。据信，在该方法中，短寿命的卤代二氟甲基碳负离子用作亲核试剂，其由二氟卡宾和卤化物阴离子可逆地产生。

  DOI：

  10.1021/ol501674n

文献信息

• Using the Thiyl Radical for Aliphatic Hydrogen‐Atom Transfer: Thiolation of Unactivated C−H Bonds
  作者：Liubov I. Panferova、Mikhail O. Zubkov、Vladimir A. Kokorekin、Vitalij V. Levin、Alexander D. Dilman

  DOI：10.1002/anie.202011400

  日期：2021.2.8

  A metal‐ and catalyst‐free thiyl‐radical‐mediated activation of alkanes is described. Tetrafluoropyridinyl disulfide is used to perform thiolation of the C−H bonds under irradiation with 400 nm light‐emitting diodes. The key C−H activation step is believed to proceed via hydrogen‐atom abstraction effected by the fluorinated thiyl radical. Secondary, tertiary, and heteroatom‐substituted C−H bonds can

  描述了无金属和无催化剂的硫代自由基介导的烷烃活化作用。四氟吡啶基二硫化物用于在400 nm发光二极管照射下对CH键进行硫键化。据信，关键的CH活化步骤是通过受氟化的噻吩基影响的氢原子提取进行的。仲，叔和杂原子取代的CH键可能参与硫醇化反应。所得的硫化物在与烯烃和杂芳烃的反应中具有作为光氧化还原活性自由基前体的广泛潜力。
• Radical Silyldifluoromethylation of Electron-Deficient Alkenes
  作者：Vyacheslav I. Supranovich、Vitalij V. Levin、Marina I. Struchkova、Alexander A. Korlyukov、Alexander D. Dilman

  DOI：10.1021/acs.orglett.7b01334

  日期：2017.6.16

  A reaction of bromo- and iododifluoromethyl-substituted silanes with electron-deficient alkenes in the presence of an N-heterocyclic carbene borane complex is described. The reaction is performed under irradiation with light-emitting diodes and proceeds via a radical chain mechanism. The resulting products, the functionalized silicon reagents, can undergo chemoselective transformations involving either

  描述了在N-杂环卡宾硼烷配合物的存在下，溴和碘代二氟甲基取代的硅烷与缺电子的烯烃的反应。该反应在发光二极管的照射下进行，并通过自由基链机理进行。所得产物，即功能化的硅试剂，可以进行涉及甲硅烷基二氟甲基片段或官能团的化学选择性转化。
• Nucleophilic Iododifluoromethylation of Aldehydes Using Bromine/Iodine Exchange
  作者：Vitalij V. Levin、Vladimir O. Smirnov、Marina I. Struchkova、Alexander D. Dilman

  DOI：10.1021/acs.joc.5b01590

  日期：2015.9.18

  A method for the iododifluoromethylation of aromatic aldehydes using (bromodifluoromethyl)trimethylsilane (Me3SiCF2Br) is described. The selective formation of the CF2I group is based on using sodium iodide, with the sodium serving as a scavenger of bromide and iodide serving as a nucleophile with respect to difluorocarbene. The primary CF2I-addition products can undergo HI-elimination or iodine/zinc exchange followed by allylation in a one-pot manner.