(2,6-dideutero-4-(tert-butyl)phenyl)boronic acid | 1431224-00-8

• 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: (2,6-dideutero-4-(tert-butyl)phenyl)boronic acid
• CAS: 1431224-00-8
• 化学式: C₁₀H₁₅BO₂
• 分子量: 180.023
• InChiKey: MNJYZNVROSZZQC-QFIQSOQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (2,6-dideutero-4-(tert-butyl)phenyl)boronic acid 在 4-叔丁基吡啶 、 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 4.25h， 生成 (Py3CH)PdII(4'-tert-butyl-2',6'-dideutero-5-fluoro-[1,1'-biphenyl]-2-yl)(I)
  参考文献：
  名称：

  A Detailed Study of Acetate-Assisted C–H Activation at Palladium(IV) Centers

  摘要：

  This report describes a detailed investigation of acetate-assisted C-H activation at Pd-IV centers supported by the tris(2-pyridyl)-methane (Py3CH) ligand. Mechanistic information about this transformation has been obtained through the following:, (i) extensive one- and two-dimensional NMR analysis, (ii) reactivity studies of a series of substituted analogues, and (iii) isotope effect studies. These experiments all suggest that C-H activation at [(Py3CH)Pd-IV(biphenyl)Cl-2)(+) occurs via a multistep process involving chloride-to-acetate ligand exchange followed by conformational and configurational isomerization and then C-H cleavage. The data also suggest that C-H cleavage proceeds via an acetate-assisted mechanism with the carboxylate likely serving as an intramolecular base. The viability of acetate-assisted C-H activation at high valent palladium has important implications for the design and optimization of catalytic processes involving this transformation as a key step.

  DOI：

  10.1021/ja401557m
• 作为产物：
  描述：

  1,6-dideutero-4-(tert-butyl)-iodobenzene 在 正丁基锂 、 硼酸三甲酯 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 4.0h， 生成 (2,6-dideutero-4-(tert-butyl)phenyl)boronic acid
  参考文献：
  名称：

  A Detailed Study of Acetate-Assisted C–H Activation at Palladium(IV) Centers

  摘要：

  This report describes a detailed investigation of acetate-assisted C-H activation at Pd-IV centers supported by the tris(2-pyridyl)-methane (Py3CH) ligand. Mechanistic information about this transformation has been obtained through the following:, (i) extensive one- and two-dimensional NMR analysis, (ii) reactivity studies of a series of substituted analogues, and (iii) isotope effect studies. These experiments all suggest that C-H activation at [(Py3CH)Pd-IV(biphenyl)Cl-2)(+) occurs via a multistep process involving chloride-to-acetate ligand exchange followed by conformational and configurational isomerization and then C-H cleavage. The data also suggest that C-H cleavage proceeds via an acetate-assisted mechanism with the carboxylate likely serving as an intramolecular base. The viability of acetate-assisted C-H activation at high valent palladium has important implications for the design and optimization of catalytic processes involving this transformation as a key step.

  DOI：

  10.1021/ja401557m

文献信息

• Deaminative coupling of benzylamines and arylboronic acids
  作者：Giedre Sirvinskaite、Julia C. Reisenbauer、Bill Morandi

  DOI：10.1039/d2sc06055h

  日期：——

  coupling of non-prefunctionalised benzylamines and arylboronic acids is reported. In this operationally simple reaction, a primary amine in benzylamine is converted into a good leaving group in situ using inexpensive and commercially available isoamyl nitrite as a nitrosating reagent. Lewis-acidic arylboronic acids are shown to replace mineral acids such as HCl or HBF4 that are conventionally used in

  报道了非预官能化苄胺和芳基硼酸的无金属脱氨基偶联。在这个操作简单的反应中，使用廉价且市售的亚硝酸异戊酯作为亚硝化试剂，将苄胺中的伯胺原位转化为良好的离去基团。路易斯酸性芳基硼酸被证明可以替代通常用于制备芳基重氮盐的无机酸，例如 HCl 或 HBF 4 。这通过以良好的产率建立新的 C-C 键，解锁了相应二芳基甲烷的形成。