2-[2,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl]pyridine | 1422450-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-[2,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl]pyridine
• 英文别名: 2-[2,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl]pyridine
• CAS: 1422450-62-1
• 化学式: C₁₉H₃₁B₂NO₄
• 分子量: 359.081
• InChiKey: CQDZNOUBNDTQCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-乙基吡啶 、 联硼酸频那醇酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 作用下， 以 正己烷 为溶剂， 反应 22.0h， 以84%的产率得到2-[2,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl]pyridine
  参考文献：
  名称：

  Synthesis of Primary and Secondary Alkylboronates through Site-Selective C(sp³)–H Activation with Silica-Supported Monophosphine–Ir Catalysts

  摘要：

  The site-selective activation and borylation of unactivated C(sp(3))-H bonds in 2-alkylpyridines to form primary and secondary alkylboronates was achieved using silica-supported monophosphine-Ir catalysts. This borylation occurs selectively at C-H bonds located gamma to the pyridine nitrogen atom. The site-selectivity of this reaction suggests that the C-H bond cleavage occurs with the assistance of a proximity effect due to N-to-Ir coordination.

  DOI：

  10.1021/ja3126239

文献信息

• Silica‐Supported Tripod Triarylphosphane: Application to Transition Metal‐Catalyzed C( <i>sp</i> ³ )H Borylations
  作者：Tomohiro Iwai、Ryo Murakami、Tomoya Harada、Soichiro Kawamorita、Masaya Sawamura

  DOI：10.1002/adsc.201301147

  日期：2014.5.5

  A silica‐supported tripod triarylphosphane (Silica‐3p‐TPP), containing a triphenylphosphane‐type core tripodally immobilized on the silica surface, allows rhodium‐ and iridium‐catalyzed C(sp3)H borylations of amide, urea and alkylpyridine derivatives. The 31P CP/MAS NMR studies for the coordination behavior of the tripod phosphane towards a rhodium complex indicate efficient site isolation of the

  的二氧化硅负载的三脚架triarylphosphane（二氧化硅-3P-TPP），含tripodally固定在二氧化硅表面上的三苯基膦型铁芯，使得铑和铱催化的C（SP 3） ħ酰胺，脲和烷基吡啶衍生物的borylations。对三脚架膦对铑配合物的配位行为的31 P CP / MAS NMR研究表明，每个膦烷中心都有效地被隔离，从而允许与金属中心进行独立的单P配位。
• Iridium-catalyzed triple C(sp3)–H borylations: construction of triborylated sp3-carbon centers
  作者：Tsuyoshi Mita、Yuto Ikeda、Kenichi Michigami、Yoshihiro Sato

  DOI：10.1039/c3cc42675k

  日期：——

  An unprecedented catalytic C(sp3)–H triborylation at a single carbon was developed with the assistance of a nitrogen directing group.

  在氮导向基团的辅助下，开发了一种在单一碳原子上进行前所未有的C(sp3)–H硼化的催化方法。
• Synthesis of Primary and Secondary Alkylboronates through Site-Selective C(sp³)–H Activation with Silica-Supported Monophosphine–Ir Catalysts
  作者：Soichiro Kawamorita、Ryo Murakami、Tomohiro Iwai、Masaya Sawamura

  DOI：10.1021/ja3126239

  日期：2013.2.27

  The site-selective activation and borylation of unactivated C(sp(3))-H bonds in 2-alkylpyridines to form primary and secondary alkylboronates was achieved using silica-supported monophosphine-Ir catalysts. This borylation occurs selectively at C-H bonds located gamma to the pyridine nitrogen atom. The site-selectivity of this reaction suggests that the C-H bond cleavage occurs with the assistance of a proximity effect due to N-to-Ir coordination.