1,3-dimethyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]imidazolidine | 1349171-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 1,3-dimethyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]imidazolidine
• 英文别名: 1,3-Dimethyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]imidazolidine
• CAS: 1349171-47-6
• 化学式: C₁₇H₂₇BN₂O₂
• 分子量: 302.225
• InChiKey: DZRQHQFNDHJOES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  24.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  联硼酸频那醇酯 、 1,3-二甲基-2-苯基咪唑烷 在 [Rh(OH)(cod)]2 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以92%的产率得到1,3-dimethyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]imidazolidine
  参考文献：
  名称：

  Rh-Catalyzed Ortho-Selective C–H Borylation of N-Functionalized Arenes with Silica-Supported Bridgehead Monophosphine Ligands

  摘要：

  Supported phosphine-Rh systems, prepared in situ from silica-supported bridgehead monophosphines and [Rh(OH)(cod)]2, have enabled ortho-selective C-H borylation for a range of arenes containing nitrogen-based directing groups. The regioselectivity was excellent with various N-directing groups, including saturated and unsaturated N-heterocycles, tert-aminoalkyl groups, and iminetype C-N double bonds. The reaction showed significant tolerance toward steric repulsion around the reacting C-H bond. This Rh catalysis complements the Jr-catalyzed orthoborylation, which is effective for arenes with oxygen-based directing groups.

  DOI：

  10.1021/ja208364a

文献信息

• Iridium-Catalyzed, Substrate-Directed C–H Borylation Reactions of Benzylic Amines
  作者：Andrew J. Roering、Lillian V. A. Hale、Phillip A. Squier、Marissa A. Ringgold、Emily R. Wiederspan、Timothy B. Clark

  DOI：10.1021/ol301635x

  日期：2012.7.6

  The iridium-catalyzed arene C–H borylation reaction of benzylic amines has been developed, which inverts the typical steric-controlled product distribution to provide ortho-substituted boronate esters. Picolylamine was found to be an ideal ligand to replace 4,4′-di-tert-butylbipyridine to induce the directing effect. Preliminary experiments are consistent with a mechanism involving dissociation of

  已开发出铱催化的苄胺的芳烃CH硼氢化反应，可转化典型的空间控制产物分布，从而提供邻位取代的硼酸酯。发现吡啶甲基胺是取代4,4'-二叔丁基联吡啶的理想配体，以诱导导向作用。初步实验与涉及半不稳定二胺配体的一种胺解离的机理是一致的。
• Rh-Catalyzed <i>Ortho</i>-Selective C–H Borylation of <i>N</i>-Functionalized Arenes with Silica-Supported Bridgehead Monophosphine Ligands
  作者：Soichiro Kawamorita、Tatsuya Miyazaki、Hirohisa Ohmiya、Tomohiro Iwai、Masaya Sawamura

  DOI：10.1021/ja208364a

  日期：2011.12.7

  Supported phosphine-Rh systems, prepared in situ from silica-supported bridgehead monophosphines and [Rh(OH)(cod)]2, have enabled ortho-selective C-H borylation for a range of arenes containing nitrogen-based directing groups. The regioselectivity was excellent with various N-directing groups, including saturated and unsaturated N-heterocycles, tert-aminoalkyl groups, and iminetype C-N double bonds. The reaction showed significant tolerance toward steric repulsion around the reacting C-H bond. This Rh catalysis complements the Jr-catalyzed orthoborylation, which is effective for arenes with oxygen-based directing groups.