3-bromo-5-(trimethylsilyl)phenylboronic acid | 950603-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-bromo-5-(trimethylsilyl)phenylboronic acid
• 英文别名: (3-Bromo-5-(trimethylsilyl)phenyl)boronic acid；(3-bromo-5-trimethylsilylphenyl)boronic acid
• CAS: 950603-55-1
• 化学式: C₉H₁₄BBrO₂Si
• 分子量: 273.009
• InChiKey: RABMSIGRISWSIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  145-147 °C
• 沸点：
  341.1±52.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-bromo-5-(trimethylsilyl)phenylboronic acid 在 一氯化碘 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以84%的产率得到3-bromo-5-iodophenylboronic acid
  参考文献：
  名称：

  Electrophilic ipso-iodination of silylated arylboronic acids

  摘要：

  Silylated functionalized arylboronic acids were converted into corresponding iodinated arylboronic acids in good yields via the electrophilic ipso-desilylation effected with iodine chloride in refluxing CHCl3. Disilylated arylboronic acids were susceptible to diiodination. In addition, the structural characterization and reactivity of a novel sterically hindered ortho-silylated diarylborinic ester were reported. The potential of selected iodinated phenylboronic acids as monomers for the SuzukieMiyaura cross-coupling polymerization was demonstrated. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.08.016
• 作为产物：
  描述：

  硼酸三甲酯 、 3,5-二溴-1-三甲基硅基苯 在 正丁基锂 、 硫酸 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 1.0h， 以86%的产率得到3-bromo-5-(trimethylsilyl)phenylboronic acid
  参考文献：
  名称：

  Electrophilic ipso-iodination of silylated arylboronic acids

  摘要：

  Silylated functionalized arylboronic acids were converted into corresponding iodinated arylboronic acids in good yields via the electrophilic ipso-desilylation effected with iodine chloride in refluxing CHCl3. Disilylated arylboronic acids were susceptible to diiodination. In addition, the structural characterization and reactivity of a novel sterically hindered ortho-silylated diarylborinic ester were reported. The potential of selected iodinated phenylboronic acids as monomers for the SuzukieMiyaura cross-coupling polymerization was demonstrated. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.08.016

文献信息

• Diastereo-, Enantio-, and <i>Z</i>-Selective α,δ-Difunctionalization of Electron-Deficient Dienes Initiated by Rh-Catalyzed Conjugate Addition
  作者：Christopher J. C. Cooze、Wesley McNutt、Markus D. Schoetz、Bohdan Sosunovych、Svetlana Grigoryan、Rylan J. Lundgren

  DOI：10.1021/jacs.1c05427

  日期：2021.7.21

  with organoboronic acid nucleophiles and aldehyde electrophiles to generate Z-homoallylic alcohols with three stereocenters. The reaction accommodates diene substrates activated by ester, amide, ketone, or aromatic groups and can be used to couple aryl, alkenyl, or alkyl aldehydes. Diastereoselective functionalization of the Z-olefin unit in the addition products allows for the generation of compounds

  金属催化的对映选择性共轭加成是立体选择性合成的高度可靠的方法；然而，由无环 π 系统的共轭芳基化引发的多组分反应很少见。这些反应通常以较差的非对映选择性进行，同时需要碱性的、对水分敏感的有机金属亲核试剂。在这里，我们展示了由四氟苯并二甲苯配体 (Ph-tfb) 支持的 Rh 催化剂能够使缺电子的 1,3-二烯与有机硼酸亲核试剂和醛对映-、非对映-和Z-选择性 α,δ-双官能化亲电试剂产生Z-具有三个立体中心的高烯丙醇。该反应适应由酯、酰胺、酮或芳基活化的二烯底物，并可用于偶联芳基、烯基或烷基醛。加成产物中Z-烯烃单元的非对映选择性官能化允许产生具有高dr和ee 的五个立体中心的化合物. 机理研究表明醛烯丙基化是决定速率的步骤，并且与类似的 Rh-烯醇化物的反应不同，δ-芳基化产生的 Rh-烯丙基物种经历醛捕获而不是质子分解，即使当水作为共溶剂存在时也是如此。这些发现应该对使用特殊的金属催化
• Light‐Induced Gold‐Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates
  作者：Jin Xie、Kohei Sekine、Sina Witzel、Petra Krämer、Matthias Rudolph、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1002/anie.201806427

  日期：2018.12.17

  photochemical gold‐catalyzed chemo‐selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts, which is orthogonal to common strategies and therefore a unique tool for synthesis of valuable biarylboronates. With this new methodology a wide array of diversely functionalized sp2‐ and sp3‐hybridized biarylboronates were obtained. Notably, the synergism of gold catalysis with copper catalysis

  Organoboron化合物是通用的合成构件。我们在此报告了一种新的策略，即光化学金催化的B，Si双功能化试剂与重氮盐的金化学选择性的Hiyama芳基化反应，该策略与常用策略正交，因此是合成有价值的联芳基硼酸酯的独特工具。通过这种新方法，获得了各种功能化的sp 2-和sp 3-杂交联芳基硼酸酯。值得注意的是，金催化与铜催化或钯催化的协同作用允许一锅式迭代C-X（杂原子）和C-C偶联，将几个简单的片段快速组装成相对复杂的分子。机理研究表明，无光敏剂的条件优于金/ Ru（bpy）3Cl 2双重催化。