triethoxy(3-fluorophenyl)silane | 53392-04-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: triethoxy(3-fluorophenyl)silane
• 英文别名: Triethoxy-(3-fluorophenyl)silane；triethoxy-(3-fluorophenyl)silane
• CAS: 53392-04-4
• 化学式: C₁₂H₁₉FO₃Si
• 分子量: 258.365
• InChiKey: BSXVNXZYPWSRPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  triethoxy(3-fluorophenyl)silane 、 1-Boc-3-碘氮杂环丁烷 在 1,1'-双(二苯基膦)二茂铁 、 四丁基氟化铵 、 palladium diacetate 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 12.0h， 以65%的产率得到tert-butyl 3-(3-fluorophenyl)azetidine-1-carboxylate
  参考文献：
  名称：

  Palladium-Catalyzed Hiyama Cross-Couplings of Arylsilanes with 3-Iodoazetidine: Synthesis of 3-Arylazetidines

  摘要：

  The first palladium-catalyzed Hiyama cross-coupling reactions of arylsilanes with 3-iodoazetidine were described. The protocol provides a convenient access to a variety of useful 3-arylazetidines which are of great interest in pharmaceutical laboratories in moderate to good yields (30%-88%). In addition, this strategy has the advantage of easy operation and mild reaction conditions.

  DOI：

  10.1021/acs.joc.9b01715

文献信息

• Nickel-Catalyzed Monofluoroalkylation of Arylsilanes via Hiyama Cross-Coupling
  作者：Yun Wu、Hao-Ran Zhang、Yi-Xuan Cao、Quan Lan、Xi-Sheng Wang

  DOI：10.1021/acs.orglett.6b02803

  日期：2016.11.4

  first example of nickel-catalyzed monofluoroalkylation of arylsilanes has been developed with readily available fluoroalkyl halides. This novel transformation has demonstrated high reactivity, broad substrate scope, excellent functional group tolerance, and mild reaction conditions. The selective activation of a relatively inert C–Si bond for slow release of aryl carbanion is the key reason for reducing

  用容易获得的氟代烷基卤化物开发了镍催化的芳基硅烷单氟烷基化的第一个例子。这种新颖的转化已显示出高反应活性，广泛的底物范围，出色的官能团耐受性和温和的反应条件。选择性活化相对惰性的C-Si键以缓慢释放芳基碳负离子是减少芳基金属种类数量的关键原因，这使该方法对于复杂生物活性分子的含氟修饰更具前景。机理研究表明，该催化循环涉及游离的氟代烷基。
• Silylarene Hydrogenation: A Strategic Approach that Enables Direct Access to Versatile Silylated Saturated Carbo‐ and Heterocycles
  作者：Mario P. Wiesenfeldt、Tobias Knecht、Christoph Schlepphorst、Frank Glorius

  DOI：10.1002/anie.201804124

  日期：2018.7.2

  by arene hydrogenation. The scope includes alkoxy‐ and halosilyl substituents. Silyl groups can be derivatized into a plethora of functionalities and find application in organic synthesis, materials science, and pharmaceutical, agrochemical, and fragrance research. However, silylated saturated (hetero‐ ) cycles are difficult to access with current technologies. The yield of the hydrogenation depends

  我们报告了一种通过芳烃加氢将易得的甲硅烷基化芳烃转化为甲硅烷基化饱和碳和杂环的方法。范围包括烷氧基和卤代甲硅烷基取代基。甲硅烷基可被衍生为多种功能，并在有机合成，材料科学以及制药，农业化学和香料研究中得到应用。但是，目前的技术很难获得甲硅烷基化的饱和（杂）循环。氢化的产率取决于硅胶添加剂的量。这种二氧化硅效应还可以显着改善以前公开的高度氟化芳烃的氢化方法（例如，氢化至全顺式C 6 H 6 F 6）。
• Process For Synthesizing Fluorinated Cyclic Aliphatic Compounds
  申请人：WESTFÄLISCHE WILHELMS-UNIVERSITÄT MÜNSTER

  公开号：US20210261478A1

  公开（公告）日：2021-08-26

  The present invention relates to a novel method for producing fluorinated cycloaliphatic compounds from the analogous aromatic compounds by hydrogenation with an Rh-carbene catalyst system.

  本发明涉及一种从类似的芳香化合物通过与Rh-卡宾催化剂系统的氢化反应产生氟化环脂化合物的新方法。
• Synthesis of (Hetero)Aryl-Functionalized Azaindoline Derivatives by Palladium-Catalyzed Domino Heck Cyclization/Hiyama Cross-Coupling
  作者：Xin-Xing Wu、Hao Ye、Ruotong Zhang、Xiaolong Xia、Yue Ding、Meihui Sun、Lei Shi、Guomin Jiang

  DOI：10.1055/a-1542-4258

  日期：2021.11

  A palladium-catalyzed domino Heck cyclization/Hiyama cross-coupling has been achieved for the synthesis of (hetero)aryl-functionalized azaindoline derivatives bearing all-carbon quaternary centers in 46–85% yields. The synthetic versatility of this protocol has been highlighted by the gram-scale synthesis and modification of aryl-containing complex bioactive molecules.

  已实现钯催化的多米诺 Heck 环化/Hiyama 交叉偶联，以 46-85% 的产率合成带有全碳四元中心的（杂）芳基官能化氮杂二氢吲哚衍生物。含芳基复杂生物活性分子的克级合成和修饰突出了该协议的合成多功能性。
• Cp*Ir‐Catalyzed C−H Arylation of 2‐Pyridones and 1‐Isoquinolinones with Arylsilanes
  作者：Tongxu Su、Heng Xu、Yi Dong

  DOI：10.1002/adsc.202400029

  日期：——

  A new Cp*Ir‐catalyzed C–H arylation of 1‐isoquinolinone and 2 pyridones to afford 6‐phenylpyridin‐2(1H)‐ones and 3‐phenylisoquinolin‐1(2H)‐ones by using arylsilanes is described in this paper. This protocol offers significant synthetic advantages, including mild reaction conditions, good functional group tolerance, a wide range of substrate applicability, and a concise approach to the core structure

  本文描述了一种新的 Cp*Ir 催化的 1-异喹啉酮和 2 吡啶酮的 C-H 芳基化反应，通过使用芳基硅烷得到 6-苯基吡啶-2(1H)-酮和 3-苯基异喹啉-1(2H)-酮。该方案具有显着的合成优势，包括温和的反应条件、良好的官能团耐受性、广泛的底物适用性以及对原小檗碱生物碱核心结构的简洁方法。为了揭示这种 Cp*Ir 催化循环的可能过程，进行了一些重要的机理研究实验。